Author: Jessica.F

Synthetic Route of 52548-14-8,Some common heterocyclic compound, 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, molecular formula is C8H7IO2, 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.

Step A: H2S04 95-98% (2.54 ml_, 0.048 mol) was added to a solution of 2-iodo-5- methylbenzoic acid (25.0 g, 0.095 mol) in MeOH (220 ml.) and refluxed for 20h. The rxn mixture was cooled with an ice bath, and 1 N aq. NaOH was added dropwise until pH 8 was reached. The org. solvent was removed in vacuo and the aq. layer was extracted with DCM (2x). The combined org. extracts were washed with sat. aq. NaHC03 (1 x) and H20 (1x), dried (Na2S04), filtered and concentrated in vacuo to give methyl 2-iodo-5-methylbenzoate as a pale yellow liquid which was used in the next step without further purification. LC-MS A: tR = 0.87 min; [M+H]+ = 259.22.

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

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOLLI, Martin; BOSS, Christoph; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi T.; WO2014/57435; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 108078-14-4, These common heterocyclic compound, 108078-14-4, name is 2-Iodo-3-methylbenzoic acid, 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 289; 292 2912-iodo-3-methylbenzoic acid ethyl ester (289)A solution of the 2-iodo-3-methylbenzoic acid (6g-0.023mol) in EtOH (15OmL) is treated with concentrated HCl (2OmL) and refluxed for 48h. After removal of the EtOH in vacuo, the residue is diluted with water (125mL) and cooled to 00C in an ice bath. The pH is adjusted to 10 with solid NaOH pellets and extracted with EtOAc (3 x 75mL). The organic extracts are washed with water (2 x 5OmL) and brine (2 x 5OmL) and dried over MgSO4. Concentrated in vacuo to give the product as a pale yellow oil. (6g, 90%).LC/MS(ES+) m/z 291

Statistics shows that 2-Iodo-3-methylbenzoic acid is playing an increasingly important role. we look forward to future research findings about 108078-14-4.

Reference:
Patent; SANOFI-AVENTIS; WO2008/151211; (2008); 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 628-77-3 as follows. Application In Synthesis of 1,5-Diiodopentane

Potassium carbonate (2.5 eq) was added to a solution of 8 (1.0 g, 1.72 mmol, 2.1 eq) and either 1,3-dibromopropane; 1,5-diiodopentane; or 1,3-bis(bromomethyl)benzene (1.0 eq) in DMF (5 mL). The resulting mixture was stirred at 75C for 3 days. After diluting with dichloromethane (25 mL), the inorganics were removed by filtration and the filtrate evaporated to dryness under reduced pressure. The residue was purified by flash chromatography to leave the products as white solids. i) diallyl 8,8′-(propane-1,3-diylbis(oxy))(2S,2’S, 11S, 11aS, 11’S, 11 a’S)-bis(2-(benzoyloxy)- 11-((tert-butyldimethylsilyl)oxy)-7-methoxy-5-oxo-2,3, 11, 11 a-tetrahydro-1H- benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate) 9a (gradient: ethyl acetate / heptane, 50/50 to 100/0 v/v). Yield 0.88 g (90%). LC/MS rt 2.17 min m/z (1227.4) M+Na.

According to the analysis of related databases, 628-77-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDIMMUNE LIMITED; HOWARD, Philip Wilson; HUTCHINSON, Ian; (102 pag.)WO2020/79239; (2020); 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 31599-61-8 as follows. SDS of cas: 31599-61-8

General procedure: In a typical experiment the catalyst (containing 2.8 lmol Pd) was placed in a stainless steel autoclave. The aryl iodide (0.2 mmol), amine (0.5 mmol), base (35 ll, 0.25 mmol) and solvent (1 ml) were transferred into it under an inert atmosphere. It was charged with carbon monoxide (30 bar or 5 bar) and heated with stirring in an oil bath at 100 C or 120 C. After cooling to room temperature the catalyst was removed by filtration and was reused without further purification if the product was soluble in the solvent. In other cases, the solid material was washed by acetone and the catalyst was dried in vacuo prior to reuse. The reaction mixture was analyzed by gas chromatography.

According to the analysis of related databases, 31599-61-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Urban, Bela; Skoda-Foeldes, Rita; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 194; 4-6; (2019); p. 302 – 306;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 33348-34-4, name is 4-Amino-3-iodobenzonitrile, 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 33348-34-4, Application In Synthesis of 4-Amino-3-iodobenzonitrile

To a 500 mL three-necked round bottom flask containing DMF (195 mL) (deoxygenated with N2 and slight vacuum) were sequentially added 4-amino-3-iodobenzonitrile (12.2 g, 50.0 mmol), pyridine 4-methylbenzenesulfonate (0.477 g, 1.9 mmol), tetraethoxysilane (13.23 g, 63.5 mmol), and ethyl 2-(2-oxocyclopentyl)acetate (12.76 g, 75.0 mmol) under N2. The reaction mixture was heated at 135 C in the dark overnight. To the mixture were added N- ethyl-N-isopropylpropan-2 -amine (26.2 mL, 150 mmol) and palladium (II) acetate (0.337 g, 1.5 mmol) under N2. The resulting mixture was cooled to 120 0C and stirred for additional 16 h. The reaction mixture was cooled to room temperature and acidified to pH ~ 5 with 1 N aq. HCl. The solvent was evaporated under reduced pressure at 60 0C. To the resulting liquid residue was added water (300 mL) and EtOAc (500 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2 x 400 mL). The combined organic layers were dried over Na2SO4, decanted and concentrated under reduced pressure to afford a dark brown liquid (22.1 g). The crude liquid was passed through a silica gel plug and eluted with 10%-40% EtOAc in hexanes. Fractions were concentrated and further purified by precipitation in DCM/hexanes to yield the title compound as a light orange solid (4.65 g). LCMS m/z = 269.2 [M + H]+; 1H NMR (400 MHz, DMSO-J6) delta ppm 1.19 (t, J = 7.12 Hz, 3H), 2.05-2.18 (m, IH), 2.54 (dd, J = 16.44, 8.45 Hz, IH), 2.64-2.85 (m, 4H), 3.52-3.63 (m, IH), 4.12 (q, J = 7.12 Hz, 2H), 7.34 (dd, J = 8.45, 1.58 Hz, IH), 7.49 (d, J = 8.45, IH), 7.85 (d, J = 0.81, IH), 11.30 (s, IH).

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-Amino-3-iodobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/78983; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 101335-11-9, A common heterocyclic compound, 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, molecular formula is C6H3ClFI, 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.

[0115] To a stirred solution of (Z)-4-(l-(4-(methoxymethoxy)phenyl)-2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)but-l-en-l-yl)benzaldehyde (12 g, 28.4 mmol, with – 10- 15% of another regioisomer) in 2-methyltetrahydrofuran (120 mL) were added 2-chloro-4- fluoro-l-iodobenzene (5.5 mL, 40.5 mmol) and KOH (45 mL, 3M aqueous solution, 142.2 mmol). The resultant mixture was degassed with argon for 10 min followed by the addition of PdCl2(PPh3)2 (0.7 g, 2.84 mmol). After stirring at 60C for 12 h, the mixture was cooled to rt and quenched with water:EtOAc (1 : 1, 100 mL). The organic layer was separated, washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The crude compound was purified by chromatography (Si02, 10% EtOAc/hexane) to afford (E)-4-(2-(2- chloro-4-fluorophenyl)- 1 -(4-(methoxymethoxy) phenyl) but- 1 -en- 1 -yl)benzaldehyde as a pale yellow solid (6.0 g, 67% with -10-15% of the other regioisomer). Major isomer: XH NMR (400 MHz, CDC1 ) delta 9.84 (s, 1H), 7.55 (d, = 8.0 Hz, 2H), 7.20 – 7.17 (m, 2H), 7.10 (d, = 8.0 Hz, 2H), 7.04 – 6.97 (m, 4H), 6.84 – 6.80 (m, 1H), 5.19 (s, 2H), 3.50 (s, 3H), 2.55 – 2.45 (m, 2H), 0.97 – 0.93 (m, 3H); MS (ESI) m/z 425.19 [M+H]+.

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZENO ROYALTIES & MILESTONES, LLC; HUANG, Peter, Qinhua; SLEE, Deborah, Helen; BUNKER, Kevin, Duane; HEGDE, Sayee, Gajanan; HOPKINS, Chad, Daniel; (76 pag.)WO2019/23481; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 35674-27-2, A common heterocyclic compound, 35674-27-2, name is 4-Iodo-3-nitrobenzoic acid, molecular formula is C7H4INO4, 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 14 Preparation of N-methyl-4-iodo-3-nitrobenzamide (Compound VII-1) 10 g (0.034 mol) 4-Iodo-3-nitrobenzoic acid (Compound VI-1) and 50 ml N,N-dimethylformamide were added into a reaction flask, stirred to dissolve, and cooled to below 10 C., and 7.5 ml (0.10 mol) sulfoxide chloride was added. After completion of the dropwise addition, the mixture was warmed to room temperature and reacted for one hour. The reaction mixture was poured into 200 ml aqueous solution of 30% methylamine with low temperature, stirred for 5 minutes to precipitate a solid, and then the mixture was added with 500 ml ice-water, stirred for 10 minutes, filtered. The solid was washed with water and dried to obtain N-methyl-4-iodo-3-nitrobenzamide (Compound VII-1), 6.5 g (0.021 mol), yield 62.3%. 1HNMR (400 MHz, DMSO-d6): delta 2.81 (d, 3H, J=4.1 Hz), 7.84 (d, 1H, 7.8 Hz), 8.23 (d, 1H, J=8.1 Hz), 8.33 (s, 1H), 8.75 (s, 1H); MS (m/z): 307 [M+H].

The synthetic route of 35674-27-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Hisun Pharmaceutical Co., Ltd.; Bai, Hua; Zhao, Xuyang; Gong, Yongxiang; Zhong, Jinqing; Zhu, Qifeng; Liu, Xiaoyu; Liu, Lifei; Zhou, Qixian; US2013/225810; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 608-28-6, name is 2-Iodo-1,3-dimethylbenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Iodo-1,3-dimethylbenzene

General procedure: Catalyst 1a22a (43 mg, 0.1 mol % of supported palladium) was added to a solution of aryl iodide (0.40 mmol, 1.0 equiv), aryltrialkoxysilane (0.80 mmol, 2.0 equiv), TBAF·3H2O (252 mg, 0.8 mmol, 2.0 equiv) in a mixture of toluene (5 mL) and H2O (50 muL). The reaction mixture was heated at 100 C for 20 h. After cooling to rt, 1a was filtered under vacuum on a 0.2 mum membrane. The catalyst was successively washed with toluene (10 mL) and Et2O (10 mL). The combined organic phases were washed with H2O (20 mL), dried with MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash-chromatography on silica gel. Catalyst 1a was dried under vacuum and can directly be used for another Hiyama coupling.

The synthetic route of 608-28-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Diebold, Carine; Derible, Antoine; Becht, Jean-Michel; Le Drian, Claude; Tetrahedron; vol. 69; 1; (2013); p. 264 – 267;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 204257-72-7, These common heterocyclic compound, 204257-72-7, name is Methyl 2-fluoro-4-iodobenzoate, 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.

To a single neck flask were added 4-bromo-2-fluorobenzene boronic acid (0.50 g, 2.28 mmol), methyl 2-fluoro-4-iodobenzene carboxylate (0.57 g, 2.06 mmol), potassium carbonate (0.95 g, 6.87 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (84 mg, 0. 11 mmol). The reaction mixture was stirred at 100 C for 1 hour and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 100/1) to give the title compound as colorless (0.39 g, 52%).

The synthetic route of 204257-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; REN, Qingyun; LIU, Xinchang; HUANG, Jianzhou; ZHANG, Yingjun; GOLDMANN, Siegfried; (342 pag.)WO2019/1396; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 401-81-0, 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 401-81-0 as follows.

General procedure: A mixture of tertiary propargylic alcohol 5 (0.13 mmol), (hetero)aryl halide (1.5 equiv), Pd(PPh3)4 (5 mol %), and K2CO3 (2.5 equiv) in CH3CN (1 mL) was heated at 90 C for 13 h. The reaction mixture was concentrated under reduced pressure to give the crude residue, which was diluted with ethyl acetate and washed with water. The organic layer was dried over MgSO4 and concentrated in vacuo to give a crude mixture, which was purified by silica gel column chromatography (hexane/ethyl acetate/dichloromethane) to afford the indolizinone 7.

According to the analysis of related databases, 401-81-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cho, Hanyang; Kim, Ikyon; Tetrahedron; vol. 68; 27-28; (2012); p. 5464 – 5480;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com