Month: December 2020

Reference of 21740-00-1,Some common heterocyclic compound, 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, molecular formula is C7H4BrIO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred mixture of acid 2-iodo-5-bromobenzoic acid (15.0 g, 45.9 mmol) in dry THF (100 mL) under argon was added neat BH3.DMS (16.0 mL, 169 mmol) dropwise over 20 minutes. The resulting mixture was heated at 65 C. for 8 hours, cooled to room temperature and quenched by the dropwise addition of water (40 mL). The reaction mixture was concentrated in vacuo. The crude alcohol was diluted with of EtOAc (300 mL), washed with 1N NaOH (2¡Á30 mL), 1N HCl (1¡Á30 mL), saturated aqueous NaHCO3 solution (1¡Á30 mL) and brine (1¡Á30 mL). The EtOAc layer was dried (MgSO4), filtered and concentrated in vacuo to give 2-iodo-5-bromobenzyl alcohol (13.8 g, 96%). 1H NMR (CDCl3): delta 7.56 (d, 1H, J=8.25 Hz), 7.54 (s, 1H), 7.04 (d, 1H, J=8.25 Hz), 4.47 (s, 2H). HPLC: Rt=3.12 min. m/z=312 M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-iodobenzoic acid, its application will become more common.

Reference:
Patent; Fink, Brian E.; Gavai, Ashvinikumar V.; Vite, Gregory D.; Han, Wen-Ching; Misra, Raj N.; Xiao, Hai-Yun; Norris, Derek J.; Tokarski, John S.; US2005/250753; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 1829-28-3,Some common heterocyclic compound, 1829-28-3, name is Ethyl 2-iodobenzoate, molecular formula is C9H9IO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar and reflux condenser, was added ethyl 2-iodobenzoate (3j, 0.14 g 0.50 mmol), Cu2O (0.060 g, 0.42 mmol), and a DMF solution of 2-Zn (0.65 M, 1.54 mL, 1.0 mmol), and the mixture was stirred at 100 C for 24 h. After being cooled to room temperature, the resulting solution was subjected to a short pad of silica gel using hexanes as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography to provide the corresponding compound 4j (0.13 g, 0.48 mmol) in 96percent yield as an yellow oil. Ethyl 2-(1,1,2,2-tetrafluorobut-3-en-1-yl)benzoate (4j) Yield: 96percent (0.13 g, 0.48 mmol); Yellow oil (hexanes/AcOEt = 15/1, Rf = 0.29); 1H NMR (CDCl3): 1.35 (t, J = 7.1 Hz, 3H, CH2CH3), 4.36 (q, J = 7.1 Hz, 2H, CH2CH3), 5.70 (d, J = 11.0 Hz, 1H, trans-CH2CHCF2), 5.86 (dt, J = 17.3, 2.2 Hz, 1H, cis-CH2CHCF2), 6.07 (ddt, J = 17.3, 11.4, 11.0 Hz, 1H, CF2CH), 7.47?7.62 (m, 4H, ArH); 13C NMR (CDCl3): 14.1 (CH2CH3), 61.9 (CH2CH3), 115.2 (tt, J = 250.2, 37.2 Hz, CF2), 116.6 (tt, J = 253.4, 36.1 Hz, CF2), 124.2 (t, J = 9.3 Hz, CH2), 126.8 (t, J = 24.4 Hz, CF2CH), 127.7 (t, J = 24.5 Hz, Ar), 128.5 (Ar), 128.7?128.9 (m, Ar), 129.7(Ar), 131.1 (Ar), 133.8 (t, J = 3.3 Hz, Ar), 168.6 (C=O); 19F NMR (CDCl3): 106.44 (s, 2F, CF2Ar), 113.42 (d, J = 11.4 Hz, 2F, CF2CH); IR (neat): 3076, 2988, 2903, 1739, 1578, 1415, 1370, 1269, 1152 cm-1 ; HRMS (FAB) calcd for [M+H]+ C13H13F4O2: 277.0852, found 277.0847.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-iodobenzoate, its application will become more common.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 391211-97-5,Some common heterocyclic compound, 391211-97-5, name is 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, molecular formula is C13H7F3INO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

EXAMPLE 1 1-3. 4-DIFLUORO-2- (2-FLUORO-4-IODO-PHENVLAMINO)-PHENVLL-2-HYDROXV-ETHANONE To a stirring suspension comprised of 3, 4-DIFLUORO-2- (2-FLUORO-4-IODO-PHENYLAMINO)- benzoic acid (1.33 g, 3.4 MMOL, which can be prepared according to the procedure of WO 02/06213) and oxalyl chloride (1.4 mL, 16 mmoles) in dichloromethane (10 mL) at ambient temperature was added 0.025 mL OF N, N-DIMETHYLFORMAMIDE. The reaction mixture was stirred for ten minutes and was concentrated in vacuo to the yellow solid 3, 4-DIFLUORO-2- (2- FLUORO-4-IODO-PHENYLAMINO)-BENZOYL chloride. The yellow solid was suspended in tris (trimethylsiloxy) ethylene (10 g, 33 MMOL) and the stirring mixture was brought to 90 C under a nitrogen atmosphere for six hours. The mixture was cooled slightly, and to it was added a solution consisting of dioxane (25 mL) and 10% aqueous hydrochloric acid (10 mL). Vigorous liberation of gas ensued and the mixture was stirred for ten minutes at 85 C. Brine (50 mL) was added and the mixture was extracted twice with ether (2 x 150 mL). The combined ether phases were washed twice with saturated aqueous sodium bicarbonate (2 x 150 mL). The ether phase was dried (MGS04) and was concentrated in vacuo to 1.4 g of an orange oil that was purified by flash chromatography. Elution with a gradient (100% hexanes to 1: 3 hexanes/ethyl acetate over 72 minutes) afforded a solid with minor impurities. The solid was dissolved in dichloromethane and vacuum filtered through silica to afford 0.135 g (9.8 % yield over two steps) of a yellow solid ; mp 128-128.5 C ; H-NMR (400 MHz; CDCl3) IB 9.80 (s, 1H), 7.40 (m, 3H), 6.77 (m, 2H), 4.83 (d, 2H, J=3.9 Hz), 3.44 (t, 1 H, J=4.1 Hz) ; 19F- NMR (376 MHz; CDCl3) 6-124. 52 (t, 1F, J=10.1 Hz), -125.27 (dd, 1F, J=10.1, 5.1 Hz), – 144.11 (d, 1F, J=7.7 Hz); MS (APCI+) 407.8 (M+1, 28), 389.8 (100); (APCI-) 405.8 (M-1, 100), 402.8 (53); IR 1662,1529, 1503,1260, 1067 CM~1 ; % C (calculated for C14H9F31NO2/FOUND) 41.30/41. 52, % H 2.23/2. 08, % N 3.44/3. 45.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/7616; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 28547-29-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 28547-29-7 name is 2-Bromo-4-iodobenzoic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

2-bromo-4-iodobenzoic acid (1 g, 3.06 mmol) was added to an eggplant-shaped flask, and dried dichloromethane was added. Thionyl chloride (433 mg, 3.67 mmol) and N,N-dimethylformamide (catalyticamount) were added dropwise. Heat to reflux and stir for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, and dimethylamine (3.1 ml, 6.06 mmol) was added dropwise. After thecompletion of the reaction, the aqueous phase was extracted with EtOAcconcentrate on a rotary evaporator and purify on a silica gel column to obtain the target compound 550mg

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4-iodobenzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 20691-72-9,Some common heterocyclic compound, 20691-72-9, name is 4-Iodo-2-nitroaniline, molecular formula is C6H5IN2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred solution of SnC? (78.0 g, 346 mmol) in concentrated HC1 (150 mL) was added 2 (25.4 g, 92.0 mmol) in three portions over 30 min at rt. The reaction mixture was heated at 70 C for 1 h and then stirred at 0 C overnight. The mixture was treated with ?0 (150 mL) and stirred for 2 h. The precipitate was collected by filtration and dried under vacuum to afford 3 (17 g, 81% yield) as a grey solid. LC-MS (ESI) m/z 235.0 (M + H)+.

The synthetic route of 20691-72-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRESIDIO PHARMACEUTICALS, INC.; LI, Leping; ZHONG, Min; WO2011/150243; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 103962-05-6, SDS of cas: 103962-05-6

Example 12: Preparation of 4-bromo-l-(4-trifluoromethoxyphenyl)-lH-imidazole. A round bottom flask was charged with 4-bromoimidazole (1.15 g, 7.81 mmol), CuI (0.07 g, 0.36 mmol), 8-hydroxyquinoline (0.05 g, 0.36 mmol), cesium carbonate (3.39 g, 10.4 mmol) and 4-trifluoromethoxyiodobenzene (1.50 g, 5.21 mmol). A 10:1 mixture of DMF (15 mL) and H2O (1.5 mL) was added to the reaction mixture, and the solution was heated to 130 0C for 4 h. The reaction mixture was then diluted with EtOAc and washed sequentially with water, ammonium chloride (saturated), water and sodium bicarbonate. The organics were dried over MgSO4, filtered and purified on a reverse phase column to give the imidazole (820 mg) as a white solid: mp 139-141 0C; ESIMS m/z 308.0 (M+H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Iodo-4-(trifluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOW AGROSCIENCES LLC; LAMBERT, William; CROUSE, Gary; SPARKS, Thomas; CUDWORTH, Denise; WO2011/17513; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6136-66-9, name is (4-Iodophenyl)(phenyl)methanone, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C13H9IO

General procedure: A two-necked flask equipped with a magnetic stirring bar was charged with Cs2CO3 (2 or 3 mmol), MCM-41-L-proline-CuI (0.1 mmol), aryl iodide (1.0 mmol), acetamidine hydrochloride (1.2 or 2 mmol) and DMF (3.0 mL) under Ar. The reaction mixture was stirred at 130 or 140 C for 20 h. After being cooled to room temperature, the mixture was diluted with CH2Cl2 (10 mL) and filtered. The catalyst was washed with distilled water (2 ¡Á 5 mL) and EtOH (2 ¡Á 5 mL) and air dried when reused in the next run. The filtrate was concentrated with the aid of a rotary evaporator and the residue was purified by column chromatography on silica gel using petroleum ether (30-60 C)/ethylacetate (10:1 to 1:1) as eluent to give the desired product 2. All the products 2a-z are known compounds.

The synthetic route of 6136-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Xue; Xiao, Ruian; You, Chongren; Yan, Tao; Cai, Mingzhong; Journal of Chemical Research; vol. 41; 6; (2017); p. 315 – 320;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 104539-21-1, name is 1-Iodo-2-(2-methoxyethoxy)ethane, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 104539-21-1, name: 1-Iodo-2-(2-methoxyethoxy)ethane

STR27 100 mg (0.240 mmol) of Compound 5 synthesised in Reference Example 4 was dissolved in 1.0 ml of anhydrous DMF. To this solution, 166 mg (1.20 mmol) of potassium carbonate and a solution of 276 mg (1.20 mmol) of 1-iodo-2-(2-methoxyethoxy)ethane in 0.5 ml of anhydrous DMF were added. This reaction mixture was stirred at room temperature for 8 hours and 25 minutes. The reaction mixture was then added to a saturated aqueous solution of sodium chloride. The mixture was then extracted with ethyl acetate. The extract layer was washed with a saturated aqueous solution of sodium chloride two times, dried over magnesium sulfate, and concentrated. The residue was chromatographed on silica gel and eluted with a mixed solvent of ethyl acetate and hexane (1:1), whereby ethyl (E)-7-[4′-fluoro-5-[2-(2-methoxyethoxy)ethoxy]-3-(propan-2-yl)biphenyl-2-yl]-3,5-dihydroxy-6-heptenoate (Compound 11) was obtained in the form of a colorless oil in a yield of 26 mg (20.9%). 1 H-NMR (300 MHz, CDCl3) delta 1.18-1.33(m, 1H), 1.21(d, J=6.8 Hz, 3H), 1.22(d, J=6.8 Hz, 3H), 1.28(t, J=7.1 Hz, 3H), 1.38-1.53(m, 1H), 2.33-2.50(m, 2H), 2.84(d, J=2.0 Hz, 1H), 3.23(hept, J=6.8 Hz, 1H), 3.39(s, 3H), 3.52-3.64(m, 2H), 3.61(d, J=2.3 Hz, 1H), 3.68-3.76(m, 2H), 3.80-3.92(m, 2H), 4.02-4.22(m, 3H), 4.18(q, J=7.1 Hz, 2H), 4.22-4.40(m, 1H), 5.19(dd, J=16.0 and 6.4 Hz, 1H), 6.51(d, J=16.0 Hz, 1H), 6.65(d, J=2.7 Hz, 1H), 6.88(d, J=2.7 Hz, 1H), 6.96-7.06(m, 2H), 7.16-7.24 m, 2H)ppm. IR (liquid film): 3456, 2964, 2932, 1736, 1602, 1512cm-1. Mass (m/z, %): 518 (M+, 52), 500 (32), 454 (93), 369 (32), 267 (32), 241 (36), 239 (43), 230 (15), 183 (20), 103 (57), 59 (100).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Iodo-2-(2-methoxyethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fujirebio Inc.; US5393780; (1995); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 116632-39-4, name is 5-Bromo-2-iodotoluene, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-2-iodotoluene

4-Bromo-1 -iodo-2-methylbenzene, 5.00 g (16.8 mmol), and N-bromosuccinimide, 3.06 g (20.2 mmol), were dissolved into 50 mL of 1,2-dichloroethane. 2,2′-Azobisisobutyronitrile, 0.28 g (1.7 mmol), was added to the above solution at 85C and the resulting mixture was stirred at this temperature for 3 hours under nitrogen atmosphere. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography to give 3.01 g (48%) of the product as a white solid. 1H-NMR (400 MHz, CDCI3): delta [ppm] = 4.54 (s, 2H), 7.13-7.16 (m, 1H), 7.63 (d, 1H), 7.73 (d, 1H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WORTMANN, Lars; SAUTIER, Brice; EIS, Knut; BRIEM, Hans; BOeHNKE, Niels; VON NUSSBAUM, Franz; HILLIG, Roman; BADER, Benjamin; SCHROeDER, Jens; PETERSEN, Kirstin; LIENAU, Philip; WENGNER, Antje, Margret; MOOSMAYER, Dieter; WANG, Qiuwen; SCHICK, Hans; (510 pag.)WO2018/172250; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 3032-81-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 3032-81-3 as follows.

EXAMPLE 4; Step A. tert-Butyl 3-{[4-((2RS)-2-{[5-chloro-1-(3,5-dichlorophenyl)-1H-indol-2-yl]carbonyl}pentyl)benzoyl]amino}propanoate; To a vial containing the title compound of Example 3 Step D (100 mg, 0.26 mmol), were added 3,5-dichloro iodobenzene (0.045 mL, 0.31 mmol), copper iodide (2.5 mg, 0.012 mmol), potassium phosphate (116 mg, 0.55 mmol), and 1,2-trans-N,N-dimethylcyclohexane diamine (0.0082 mL, 0.05 mmol). The reaction mixture was placed under a nitrogen atmosphere, and anhydrous toluene (0.300 mL, deoxygenated via nitrogen sparge), was added. The vial was then capped and placed in a pre-heated oil bath (110¡ã C.) and stirred rapidly for 20 h. The mixture was allowed to cool to room temperature, then was filtered through a silica gel plug, eluting with EtOAc. The filtrate was concentrated in vacuo: LCMS B, tr=3.10 min, m/z 528.1 [M+H]+. The crude adduct was dissolved in 1,4-dioxane (1.5 mL). 2 N aq. LiOH (1.3 mL, 2.6 mmol) was added, and the resultant mixture was stirred at 50¡ã C. for 1 h. The mixture was allowed to cool to room temperature whereupon it was quenched by the addition of 2 N aq. HCl. The aqueous phase was extracted with EtOAc, and the organic phase was dried over Na2SO4 and concentrated in vacuo. To the crude carboxylic acid obtained above were added EDC (150 mg, 0.78 mmol), HOBt (105 mg, 0.78 mmol), and beta-alanine tert-butyl ester hydrochloride (141 mg, 0.78 mmol). The resultant mixture was dissolved in DMF (2 mL), DIEA (0.275 mL, 1.56 mmol) was added, and the reaction mixture was stirred at 50¡ã C. for 18 h. The reaction mixture was quenched by addition of sat. aq. NH4Cl, and the aqueous phase was extracted with EtOAc. The organic phase was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 70percent, then 70 to 100percent EtOAc in hexanes) provided the title compound: LCMS B, tr=3.01 min, m/z 663.1 [M+H]+; 1H NMR (500 MHz, CDCl3) delta 7.67 (d, J=2.0 Hz, 1H), 7.66 (s, 1H), 7.65 (d, J=8.0 Hz, 2H), 7.46 (t, J=7.0 Hz, 1H), 7.27-7.21 (m, 4H), 6.96 (d, J=8.0 Hz, 2H), 8.87 (t, J=5.5 Hz, 1H), 3.65 (q, J=6.0 Hz, 2H), 3.64-3.59 (m, 1 H), 3.04 (dd, J=14.0, 9.0 Hz, 1H), 2.83 (dd, J=14.0, 5.5 Hz, 1H), 2.52 (t, J=6.0 Hz, 1H), 1.80-1.73 (m, 1H), 1.59-1.52 (m, 1H), 1.44 (s, 9H), 1.41-1.33 (m, 2H), 0.92 (t, J=7.0 Hz, 3H).

According to the analysis of related databases, 3032-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kim, Ronald M.; Bittner, Amy R.; Sinz, Christopher Joseph; Parmee, Emma R.; US2007/88071; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com