Month: February 2021

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13421-00-6, name is 5-Chloro-2-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Chloro-2-iodobenzoic acid

General procedure: A dry sealable vial was charged with sulfonimidamide 4a (368 mg, 2.00 mmol), 2-iodobenzoic acid (494 mg, 2.00 mmol), CuI (76 mg, 0.40 mmol), and K2CO3 (690 mg, 5.00 mmol) in anhyd DMF (5.0 mL). After heating to 100 C for 2 h, the heterogeneous mixture was cooled to r.t. The mixture was diluted with water (10 mL), acidified with 2 M HCl and extracted with EtOAc (3 ¡Á 30 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by CombiFlash chromatography (silica gel, n-hexane/EtOAc, 6:4) to afford the desired product 7a as a cream solid; yield: 633 mg (90%).

The synthetic route of 13421-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sen, Indira; Sasmal, Swarnendu; Hall, Roger G.; Pal, Sitaram; Synthesis; vol. 48; 21; (2016); p. 3743 – 3752;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 101066-87-9, name is 4-Iodo-2-(trifluoromethyl)benzonitrile, its 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. Safety of 4-Iodo-2-(trifluoromethyl)benzonitrile

[0443] A suspension of trans-1-(4-methoxybenzyl)hexahydropyrano[3,4-d]imidazol-2(3H)-one [racemic (¡À)] (0.25 g, 0.95 mmol), 4-iodo-2-(trifluoromethyl)benzonitrile (0.28 g, 0.95 mmol), trans-N,N?-dimethylcyclohexane-1,2-diamine (0.032 g, 0.29 mmol) and potassium carbonate (0.395 g, 2.86 mmol) in toluene (15 mL) was degassed for 30 min in a microwave vial. CuI (0.009 g, 0.05 mmol) was added and the vial was sealed with an aluminum cap. The sealed vial was kept in a preheated oil bath at 110 C. and stirred for 12 h. The reaction mixture was cooled to RT, filtered through a pad of celite, and filtrates were concentrated under reduced pressure to give a black residue. The residue was purified by column chromatography on silica gel (dichloromethane/methanol=100:0 to 99:1) to give the title compound (0.17 g, 41.0%) as an off white solid. LCMS: m/z 432.1 [M+H]+; 1H NMR (400 MHz, CDCl3) delta 7.80-7.74 (m, 2H), 7.54 (d, 1H), 7.20 (d, 2H), 6.84 (d, 2H), 4.50 (d, 1H), 4.40-4.30 (m, 2H), 4.15-4.05 (m, 1H), 3.80 (s, 3H), 3.65 (ddd, 1H), 3.50-3.20 (m, 2H), 3.10 (ddd, 1H), 1.90 (d, 1H), 1.72-1.68 (m, 1H).

The synthetic route of 4-Iodo-2-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bock, Mark Gary; Chikkanna, Dinesh; Gerspacher, Marc; Khairnar, Vinayak; Lagu, Bharat; Pandit, Chetan; US2014/329858; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 31827-94-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 31827-94-8, name is 2-Bromo-1-(4-iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows.

Step A18b. A solution of the compound from step A18a (512 mg, 1.86 mmol) in (( (5 mL) was treated with DIPEA (0.45 mL, 2.58 mmol) and MsCl (0.16 mL, 2.07 mmol) for 2 hours at 0 C before being partitioned (CH2Cl2-water). The organics were washed with brine, dried ( a2S04), filtered and evaporated to give the crude desired compound as a colorless oil (725 mg), which was used directly in the next step. ESIMS m/z = 254.20 [M-Boc+2H]+. Step A18c. A solution of the compound from step A18b (1.82 mmol at most) in DMF (5 mL) was treated with 15-crown-5 (80 mg, 0.36 mmol) and al (1.36 g, 9.1 mmol) in the presence of K2CO3 (1.12 g, 8.12 mmol) at 90 C overnight before being cooled down and partitioned (EtO Ac -water). The organics were washed with water, brine, dried ( a2S04), filtered and evaporated. The residue was purified by chromatography (silica, hexanes- ethyl acetate) to give the desired compound as a colorless oil (396 mg, 56%) containing an isomeric impurity. ESIMS m/z = 386.10 [M+H]+. Step A18d. A solution of the compound from step A18c (516 mg, 1.34 mmol) in toluene (10 mL) was treated with totally 4 portions of Bu4SnH (0.36 mL, 1.34 mmol) and AIBN (22 mg, 0.134 mmol) for 12 hours at 110 C before being cooled down and evaporated. The residue was purified by chromatography (silica, hexanes-ethyl acetate) to give the desired compound as a colorless oil (177 mg, 51%) as a single isomer. ESIMS m/z = 260.10 [M+H]+. Step A18e. A solution of the compound from step A18d (170 mg, 0.655 mmol) in CH2CI2 (3 mL) was treated with DAST (0.18 mL, 1.32 mmol) at 0 C for 1 hours before being quenched with aqueous aHC03 dropwisely and partitioned (CH2Cl2-water). The organics were washed with brine, dried ( a2S04), filtered and evaporated. The residue was purified by chromatography (silica, hexanes-ethyl acetate) to give the desired compound as a colorless oil (177 mg, 51%). ESIMS m/z =260.10 [M+H]+. Step A18f. The desired compound was prepared from the compound from step A18e using procedures similar to that described in Intermediate A7. ESIMS m/z = 472.11 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1-(4-iodophenyl)ethanone. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; NOVARTIS AG; QIU, Yao-ling; CAO, Hui; PENG, Xiaowen; GAO, Xuri; OR, Yat, Sun; SWEENEY, Zachary, Kevin; WO2015/17382; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 138385-59-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 138385-59-8, name is 4-Iodo-2,6-dimethylaniline hydrochloride belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(Z)-Methyl 3-(4-amino-3,5-dimethylphenyl)-2-(benzyloxycarbonyl)acrylate.; A 2 L round bottom flask was charged 4-iodo-2,6-dimethylbenzenaminehydrochloride salt (55 g, 194 mmoles), methyl 2-(benzyloxycarbonyl)acrylate (59.2 g, 252 mmoles), tetrabutylammonium chloride (59.2 g, 213 mmoles), palladium (II) acetate (4.34 g, 19.4 mmoles), and tetrahydrofuran (1.2 L, degassed by a flow of nitrogen for 30 min). The mixture was stirred so that a suspension was formed and then degassed by a flow of nitrogen for 30 min. Triethylamine (1 10 mL, 789 mmoles) was added and the resulting mixture was heated at reflux for 3 h. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, washed with tetrahydrofuran (2 x 100 mL), and concentrated. The residue was dissolved in dichloromethane, washed with water (3X) and brine (2X), dried over sodium sulfate, and concentrated. Flash chromatography (silica gel, using 1 :9 ethyl acetate/dichloromethane) gave a tan solid. The solid was recrystallized from warm methanol (210 mL) and water (100 mL). The mixture was held at room temperature overnight, then at 0C for 2 h, and finally at -15C for 2 h. The resulting solid was filtered, washed with ice cold 1 : 1 methanol/water, and dried under high vacuum overnight to give 44.7 g (65%) as a light tan solid which was a mixture of Z/E isomers (73:27). XH-NMR (DMSO-d6) delta, 2.05 (s, 6 H), 3.61 (s, 0.8 H), 3.68 (s, 2.2 H), 5.00 (s, 0.54 H), 5.13 (s, 1.46 H), 5.24 (s, 2 H), 7.40-7.21 (m, 8 H), 8.51 (s, 0.27 H), 8.79 (s, 0.73 H); 1 jC-NMR (DMSO-d6) delta 17.8, 51.7, 65.3, 1 19.4, 120.0, 120.3, 127.3, 127.7, 128.3, 130.9, 135.8, 137.2, 146.9, 154.7, 166.0.

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, 4-Iodo-2,6-dimethylaniline hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHATURVEDULA, Prasad V.; DUBOWCHIK, Gene M.; MACOR, John E.; WO2011/123232; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 156150-67-3 as follows. Quality Control of 2-Chloro-1-fluoro-4-iodobenzene

To the stannane (0.39 g, 0.95 mmol) in DMF (10 ml) was added the 2-chloro-4-fluoroiodobenzene (0.73 g, 2.86 mmol), Cul (0.19 g, 1.05 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.11 g, 0.095 mmol). The reaction was stirred at RT under N2 for 21 h. The reaction mixture was added to Et2O and the heterogeneous solution filtered through a bed of celite, washing with EtOAc. The filtrate was washed with water and brine and dried (MgSO4). Filtration and evaporation of the solvent in vacuo afforded a residue that was preadsorbed on silica gel. Purification by silica gel chromatography (4% EtOAc/hexane) yielded the arylacrylate (0.19 g, 78%), which was used directly in the next step.

According to the analysis of related databases, 156150-67-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Corporation; US6391865; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 162358-07-8, A common heterocyclic compound, 162358-07-8, name is 1-(2-Iodoethyl)-4-octylbenzene, molecular formula is C16H25I, its 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 16 Production of diethyl acetamido-2-(4-octylphenyl)ethylmalonate (8) [Step (H)] To a solution of diethyl acetamidomalonate (277 g) and sodium ethylate (86.6 g) in anhydrous ethanol (850 ml) is added a solution of 2-(4-octylphenyl)ethyl iodide (7) (146 g) in anhydrous tetrahydrofuran (533 ml), and the mixture is refluxed under heating for 6 hr. The reaction mixture is concentrated and partitioned between water and hexane, and the hexane layer is washed three times with water. The obtained hexane layer is dried over anhydrous magnesium sulfate and concentrated. The residue is recrystallized from hexane to give the title compound (8) as colorless crystals. The resulting Compound (8) has the same physico-chemical characteristics as indicated in Example 7.

The synthetic route of 162358-07-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abel, Stephan; Fujita, Tetsuro; Hirose, Ryoji; Jordine, Guido; Mishina, Tadashi; US2002/72635; (2002); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 103440-55-7, name is Methyl 2-iodo-6-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 103440-55-7

Methyl 2-iodo~6-methybenzoate (158) (2.00 g, 7.245 mmoi) and NBS (1.418 g, 7.969 mmol) were stirred in chiorobenzene (50 mL) and benzoyl peroxide (75% w/w, 0.234 g, 0.724 mmol) was added. The reaction was stirred at 90 C for 18 hours, cooled to room temperature, filtered and the precipitate was washed with cyclohexane (4×10 mL). The combined filtrates were evaporated, and the resulting brown oil was diluted with THF (50 mL). Aqueous ammonia solution (20 mL) was added, and the mixture was stirred vigorously for 17 hours. The mixture was diluted with water (20 mL) and the THF was removed in vacuo. DCM (150 mL) was added, the layers were separated and the aqueous layer was extracted with DCM (2×100 mL), the combined organics were washed with brine (100 mL), dried (MgS04) and filtered. Silica gel was added and the voiatiles were removed in vacuo to give the crude material absorbed onto silica gel. The material was purified by silica gel chromatography (Biotage Isolera, 40 g Si cartridge, 0- 00% EtOAc in petroleum benzine 40-60 C, then 0-20% methanol in EtOAc) to give the title compound (159) (0.757 g, 40% yield) as a beige solid; 1H NMR (400 MHz, CDCI3) delta 7.93 (dd, J = 7.8, 0.7 Hz, 1 H), 7.46 (dd, J = 7.5, 0.8 Hz, 1 H), 7.26 – 7.21 (m, 1 H), 7.10 (br s, 1 H), 4.37 (d, J = 0.6 Hz, 2H). LCMS Method C: rt 5,06 min; m/z 260.0 [M+Hf .

According to the analysis of related databases, 103440-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; DEVLIN, Mark Graeme; STREET, Ian Philip; TONG, Warwick Bonner; WO2014/27199; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 98-61-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 98-61-3, name is 4-Iodobenzenesulfonyl chloride belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5.1.11 N-[(5-Isobutyl-1-phenyl-1H-pyrazol-3-yl)methyl]-4-iodobenzenesulfonamide (9d) Triethylamine (32.6 muL, 0.234 mmol) was added at 0 C to a solution of (5-isobutyl-3-aminomethyl-1-phenyl)pyrazole (48.7 mg, 0.212 mmol) in dichloromethane (1.0 mL). The solution was stirred for 5 min, and mixed with a solution of 4-iodobenzenesulfonyl chloride (68.2 mg, 0.223 mmol) in dichloromethane. Subsequently, the solution was warmed to room temperature, and stirred for 1 h. Then, water and a saturated sodium hydrogen carbonate solution were added to the solution before extraction with dichloromethane. The organic layer thus formed was dried over magnesium sulfate, concentrated in vacuo, and purified by column chromatography (hexane:EtOAc = 3:1 ? 2:1) to afford the title compound (86.3 mg, 82.0%). 1H NMR (400 MHz, CDCl3) delta 7.76 (d, J = 8.16 Hz, 2H), 7.53 (d, J = 8.24 Hz, 2H), 7.46-7.38 (m, 3H), 7.23 (d, J = 7.60 Hz, 2H), 5.95 (s, 1H), 5.72 (br, 1H), 4.18 (d, J = 5.80 Hz, 2H), 2.40 (d, J = 7.16 Hz, 2H), 1.75-1.68 (m, 1H), 0.81 (d, J = 6.60 Hz, 6H); 13C NMR (100 MHz, CDCl3) delta 147.6, 144.4, 139.9, 139.5, 138.1, 129.2, 128.7, 128.2, 125.7, 104.8, 99.7, 41.0, 35.0, 28.3, 22.4.

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, 4-Iodobenzenesulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kim, Jung Hyun; Keum, Gyochang; Chung, Hesson; Nam, Ghilsoo; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 665 – 672;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 16355-92-3, The chemical industry reduces the impact on the environment during synthesis 16355-92-3, name is 1,10-Diiododecane, I believe this compound will play a more active role in future production and life.

2-Picoline (0.30 mL, 3.1 mmol) and 1,10-diiododecane (13.0 g, 33 mmol) were dissolved in acetone (20 mL) with a 50 mL flask equipped with a condenser. The solution was heated to reflux at 60C for 4 days. The solution was dropped into hexane (300 mL), and then a yellow precipitate was obtained. The precipitate was recovered and dried to obtain the product 4 as yellow powder (yield 1.3 g, 87%). 1H NMR (500MHz, DMSO-d6): delta 8.96 (d, J=5.1Hz, 1H), 8.44 (t, J=7.8Hz, 1H), 8.02 (d, J=7.9Hz, 1H), 7.94 (t, J=6.8Hz,1H), 4.51 (t, J=7.8Hz, 2H), 3.25 (t, J=6.8Hz, 2H), 2.82 (s, 3H), 1.85-1.79 (m, 2H), 1.75-1.69 (m, 2H), 1.36-1.22 (m, 12H).

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, 1,10-Diiododecane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hashidzume, Akihito; Kuse, Akihiro; Oshikiri, Tomoya; Adachi, Seiji; Yamaguchi, Hiroyasu; Harada, Akira; Tetrahedron; vol. 73; 33; (2017); p. 4988 – 4993;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, molecular formula is C7H4F3IO, 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. Application In Synthesis of 1-Iodo-4-(trifluoromethoxy)benzene

Step A: Preparation of 2-bromo-5-(4-(trifluoromethoxy)phenyl)pyridine. [00137] To a microwave vial equipped with a magnetic stir bar were added (6-bromopyridin-3- yl)boronic acid (1.37 g, 6.77 mmol), l-iodo-4-(trifluoromethoxy)benzene (1.5 g, 5.21 mmol) and DMF (11.9 mL), followed by K2C03 (2.52 g, 18.2 mmol) and water (2.98 mL). The reaction mixture was stirred under N2 for 5 min and treated with Pd(PPh )4 (16.05 mg, 0.014 mmol). The reaction vessel was capped, placed in a Biotage Initiator microwave reactor for 1 h at 120 ¡ãC, with external IR-sensor temperature monitoring from the side of the vessel. The cooled reaction mixture was filtered through a pad of Celite? rinsing with EtOAc (100 mL), and the filtrate was washed successively with saturated aqueous NaHC03 (50 mL), water (3 x 50 mL), and brine (50 mL). The organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by column chromatography (Si02, 0-M0 EtOAc in hexanes) to give the title compound (1.07 g, 63percent) as an off-white solid: IR (Thin Film) 3036, 1453, 1210, 1167 cm”1; 1H NMR (400 MHz, CDC13) delta 8.57 (dd, J = 2.6, 0.8 Hz, 1H), 7.71 (dd, J= 8.2, 2.6 Hz, 1H), 7.63 – 7.54 (m, 3H), 7.38 – 7.29 (m, 2H); 19F NMR (376 MHz, CDC13) delta -57.83; HRMS-ESI (m/z) [M+H]+ calcd for Ci2H8BrF3NO, 317.9736; found, 317.9735.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103962-05-6, its application will become more common.

Reference:
Patent; DOW AGROSCIENCES LLC; LOSO, Michael R.; GUSTAFSON, Gary D.; KUBOTA, Asako; YAP, Maurice C.; BUCHAN, Zachary A.; STEWARD, Kimberly M.; SULLENBERGER, Michael T.; HOEKSTRA, William J.; YATES, Christopher M.; WO2015/160665; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com