Tag: M.W=200-300

2401-21-0, The chemical industry reduces the impact on the environment during synthesis 2401-21-0, name is 1,2-Dichloro-3-iodobenzene, I believe this compound will play a more active role in future production and life.

PREPARATION 1 A mixture of p-aminoacetophenone (20 g), pyridine (11.7 g), and iodobenzene dichloride (40 g) in tetrahydrofuran (300 ml) was stirred for 5 hours at 0¡ã C. The insoluble materials were filtered, and the filtrate was concentrated under reduced pressure. The residue obtained was crystallized from ethanol to give colorless crystals of 4′-amino-3′-chloroacetophenone (20.1 g). IR (Nujol): 3420, 3340, 3230, 1665, 1635, 1590 cm-1.

The chemical industry reduces the impact on the environment during synthesis 1,2-Dichloro-3-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4866091; (1989); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

52548-14-8, The chemical industry reduces the impact on the environment during synthesis 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 5-methyl-2-iodobenzoic acid (3.0 g, 11 .4 mmol) in toluene (150 mL), SOCl2 (8.35 mL, 114 mmol) was added and the mixture was heated at 100C for 3 hours. Thesolvent was concentrated in vacuum and the residue was co-evaporated from toluene twice to give the title compound as a grey solid. Yield (3.2 g, 100%). 1H NMR (400 MHz, CDCl3): 6 2.42 (s, 3H), 7.09 (dd, 1 H), 7.90 (d, 1 H), 7.92 (d, 1 H).

The chemical industry reduces the impact on the environment during synthesis 2-Iodo-5-methylbenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ROTTAPHARM SPA; STASI, Luigi Piero; ROVATI, Lucio; WO2013/139730; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

39998-81-7, 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. 39998-81-7, name is 2-Fluoro-4-iodo-1-methylbenzene, A new synthetic method of this compound is introduced below.

Methyl-2-fluoro-4-iodo benzoate (Reagent G) A solution of 2-fluoro-4-iodo toluene (5 g, 26.6 mmol) in pyridine (2 mL) and water (20 mL) was treated with potassium permanganate (16.6 g, 105 mmol) and heated at 150 C. overnight. The reaction mixture was then cooled to room temperature and filtered and the filtrate was extracted with hexane. The aqueous phase was acidified with 10% hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was dissolved in 20 mL of methanol, treated with concentrated sulfuric acid (1 mL) and refluxed overnight. The volatiles were distilled off in vacuo and the residue was dissolved in diethyl ether, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent afforded the title compound as an oil (0.26 g, 5%). 1H NMR (300 MHz, CDCl3):delta 7.60 (m, 4H), 3.93 (s, 3H).

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; Allergan Sales, Inc.; US6252090; (2001); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

116632-39-4, The chemical industry reduces the impact on the environment during synthesis 116632-39-4, name is 5-Bromo-2-iodotoluene, I believe this compound will play a more active role in future production and life.

A Schienk tube was charged with compound 480 (402 mg, 1.31 MMOL) in 1,4-dioxane (3.0 mL), 5-BROMO-1-IODO-TOLUENE (358 mg, 1.19 MMOL), sodium tert-butoxide (160 mg, 1.67 MMOL), PD2 (dba) 3 (27 mg, 0.03 MMOL), and rac-BINAP (28 mg, 0.045 MMOL). The tube was capped with a rubber septum, flushed with argon for 5 min, and then stirred at 100 C for 72 h. The reaction mixture was allowed to cool to RT, and then poured into a mixture of water and EtOAc. The aqueous phase was extracted twice with more EtOAc. The combined organic phases were washed with brine, dried (MGSO4), filtered and concentrated in vacuo. The crude product was purified by chromatography eluting with petroleum ether/EtOAc 4: 1 to afford the title compound as yellow oil. 13C NMR (CI3) 8 195.4, 160.6, 147.7, 141.9, 137.7, 134.3, 134.0, 133.9, 133.4, 132.6, 131.6, 130.3, 130.0, 124.5, 117.6, 117.6, 116.1, 112.9, 111.0, 81.7, 67.0, 21.3, 17.8

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-2-iodotoluene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; LEO PHARMA A/S; WO2005/9940; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

64248-58-4, 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. 64248-58-4 name is 1,2-Difluoro-4-iodobenzene, 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.

3,4-difluoro-iodobenzene (100mg, 0.41mmoL) and piperazine (32mg, 0.41mmoL) were mixed in 5mL of dioxane, under a nitrogen atmosphere, followed by triethylamine (54mg, 0.45mmoL), 2.5 mg of X-phos (2- dicyclohexyl-P-2 ‘, 4′, 6’-triisopropyl biphenyl) and 2.5mg of Pd2 (dba) 3 (tris (dibenzylideneacetone) dipalladium) , then stirred at room temperature for 3 hours. Then vacuum to spin dioxane was added 20mL of water and 20mL of ethyl acetate, the organic phase was dried over sodium sulfate, spin dry and separate living give 37mg of product. The above product (37mg, 0.19mmoL) and piperazine (40mg, 0.55mmol), potassium carbonate (60mg, 0.43 mmol) were mixed in N, N- dimethylacetamide in a microwave at 150 stirred for 2 hours, and then spin to N, N- dimethylacetamide, purified by column to give (3-fluoro-4- (piperazin-1-yl) phenyl) dimethyl phosphine oxide (40mg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Difluoro-4-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Hansoh BioMedical Co., Ltd.; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; Yang, Fei; Zhang, Xiuchun; Sun, Xingyi; Wei, Mingsong; Wang, Chunjuan; Tong, Chaolong; Li, Chenghai; Bao, Rudi; Yu, Hongping; Xu, Yaochang; (52 pag.)CN105712928; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

101335-11-9, 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. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-chloro-4-fluoro-l-iodobenzene (10.0 g, 39.0 mmol) in dry THF (150 niL) was added /-PrMgCl (29.3 niL, 2.0 N, 58.5 mmol) dropwise at 0 C . After stirring for 1 hr at 0 C , the reaction was warmed to room temperature and stirred for 2 h. 1,4-cyclohexanedione monoethylene acetal (4.87 g, 31.2 mmol) was added and the reaction was stirred at room temperature for 12 h. Water (100 mL) was added and the mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic phases were washed with brine (100 mL), then dried over Na2SO4. After concentration in vacuo, the crude material was purified by column chromatography (petroleum ethe?ethyl acetate = 5:1) on silica gel to give the desired product as a white solid (5.38 g, 48%). 1H NMR (400 MHz, CDCl3): delta 7.61-7.57 (m, IH), 7.14-7.11 (m, IH), 6.99- 6.94 (m, IH), 4.00-3.95 (m, AzU), 2.63-2.57 (m, IH), 2.42-2.36 (m, 2H), 2.17-2.10 (m, 2H), 2.05-2.01 (m, 2H), 1.72-1.69 (m, 2H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SEPRACOR INC.; BURDI, Douglas; SPEAR, Kerry, L.; HARDY, Larry, Wendell; WO2010/114971; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 3058-39-7, name is 4-Iodobenzonitrile, molecular formula is C7H4IN, 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. 3058-39-7

To phenol (1.23 g, 13.10 mmol), copper(I) iodide (333 mg, 1.75 mmol), cesium carbonate (5.69 g, 17.47 mmol), 4-iodobenzonitrile (2.00 g, 8.73 mmol) and N,N-dimethylglycine hydrochloride (366 mg, 2.62 mmol) under nitrogen was added degassed 1,4-dioxane (10.0 mL). The whole mixture was heated at 90 C. for 88 hours. The cooled mixture was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2¡Á100 mL). The organic layers were combined and washed with brine (100 mL) and dried with Na2SO4 and concentrated in vacuo. The crude material was purified by column chromatography EtOAc/Hex (1:12?1:8) to give the pure product as a white solid (quantitative yield). 1H NMR (300 MHz, CDCL3) delta(ppm): 7.00 (2H, d, J=9.1 Hz), 7.06 (2H, d, J=7.6 Hz), 7.23 (1H, t, J=7.2Hz), 7.41 (2H, t, J=8.1 Hz), 7.59 (2H, d, J=9.1 Hz). 13C NMR (75 MHz, CDCL3) delta(ppm): 105.9, 118.0 (CH), 119.0, 120.5 (CH), 125.3 (CH), 130.4 (CH), 134.2 (CH), 154.9, 161.8. MS (FAB+): 196 (MH+). HRMS for C13H9NO (MH+): calculated: 196.0762; found 196.0780.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3058-39-7, its application will become more common.

Reference:
Patent; UNIVERSITY OF NOTRE DAME DU LAC; US2010/261673; (2010); A1;,
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. 82998-57-0, name is 3-Iodo-4-methylbenzoic acid, A new synthetic method of this compound is introduced below., 82998-57-0

Step 1: To a solution of 3-iodo-4-methyl-benzoic acid (10.0 g, 38.2 mmol) in methanol (70 ml) is added concentrated sulfuric acid (0.5 ml). The reaction mixture is heated at 70C for 48 hours, cooled to room ambient temperature and then concentrated. After that, ethyl acetate (100 ml) and aqueous NaHCO3 (saturated, 100 ml) solution are added to the residue. The organic layer is separated and washed again with aqueous NaHCO3 (saturated, 100 ml) solution. The organic layer is separated, dried over anhydrous Na2SO4 and concentrated to yield 3-iodo-4-methyl-benzoic acid methyl ester 1. It is used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) delta 8.31 (s, 1 H), 7.87 (d, 1 H, J = 8.4 Hz), 7.48 (d, 1 H, J = 8.4 Hz), 3.85 (s, 3 H), 3.35 (s, 3H); LC-MS m/z: 277.0 (M+1).

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; Novartis AG; DIERKS, Christine; WARMUTH, Markus; WU, Xu; (20 pag.)EP2162190; (2016); B1;,
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. 82998-57-0, name is 3-Iodo-4-methylbenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 82998-57-0

i) Production of 3-iodo-N,4-dimethylbenzamide 3-Iodo-4-methylbenzoic acid (9.84 g) was dissolved in THF (50 ml) and thionyl chloride (4 ml) and DMF (0.05 ml) were added. The mixture was heated under reflux for 3 hrs. The reaction mixture was concentrated under reduced pressure to give 3-iodo-4-methylbenzoyl chloride (10.18 g) as a brown powder.

The synthetic route of 82998-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; Kusaka, Masami; EP1348706; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 660-49-1, name is 3-Fluoro-5-iodoaniline, 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. 660-49-1

Dissolve 3-fluoro-5-iodoaniline (600mg, 2. 53MMOL) (prepared as described in published PCT International Application W096/23783 A1, published August 8,1996), METHANESULFONYL chloride (896mg, 7. 83MMOL), triethylamine (1. 91G, 18.9mmol), and N, N-dimethylamino-4-pyridine (31MG, 0. 253MMOL) in CH2CK (lOmL) and stir at room temperature overnight. Dilute with L. OON aqueous HC1 (20ML) and extract into ethyl acetate. Dry (MGS04) and concentrate organics to a yellow solid. Dissolve solid in THF (50ML) and add L. OM tetrabutylammonium fluoride (2.8mL). Heat to reflux for 3. 5h. Cool to room temperature, dilute with H20, and extract into ethyl acetate. Dry (MGS04) and concentrate organics. Chromatograph on silica gel (40g), eluting with 20% to 35% ethyl acetate/hexanes affords 618MG (78%) of the title compound as a white solid. MS (ES) 314 (M-H) ; HPLC shows 100% purity.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 660-49-1.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/52847; (2004); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com