Tag: M.W=100-200

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. 3814-30-0 name is (Bromomethyl)cyclopentane, 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. 3814-30-0

EXAMPLE 51A Methyl 3-cyclopentyl-2-methyl-2-phenylpropanoate A solution of lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 3.04 mL, 3.04 mmol, 1 equiv) under a N2 atmosphere was cooled to 0 C. and treated with a solution of methyl 2-phenylpropionate (0.500 g, 3.04 mmol, 1 equiv) in dry tetrahydrofuran (2 mL). The reaction was stirred at 0 C. for 2 hrs, then cooled to -78 C. and treated with hexamethylphosphoric triamide (0.4 mL) and bromomethylcyclopentane (0.745 g, 4.568 mmol, 1.5 equiv). Stirred the reaction at -78 C. and allowed the bath to slowly warm to room temperature overnight. After 15 hrs, the reaction mixture was quenched with 10% aq NH4Cl (50 mL) and extracted with ethyl acetate (100 mL). The organic extract was washed with H2O (50 mL) and brine, then dried over Na2SO4, filtered, and concentrated by rotary evaporation. The residue was purified by SiO2 flash chromatography with 2:3 dichloromethane/hexanes to give the product as colorless oil (1.38 g, 5.60 mmol, 92%). 1H NMR (300 MHz, DMSO-d6): delta ppm 0.90-1.12 (m, 2H) 1.32-1.72 (m, 10H) 1.97-2.12 (m, 2H) 3.58 (s, 3H) 7.19-7.35 (m, 5H); MS (APCI+) m/z 247 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Bromomethyl)cyclopentane, and friends who are interested can also refer to it.

Reference:
Patent; Hutchinson, Douglas K.; Bellettini, John R.; Betebenner, David A.; Bishop, Richard D.; Borchardt, Thomas B.; Bosse, Todd D.; Cink, Russell D.; Flentge, Charles A.; Gates, Bradley D.; Green, Brian E.; Hinman, Mira M.; Huang, Peggy P.; Klein, Larry L.; Krueger, Allan C.; Larson, Daniel P.; Leanna, M. Robert; Liu, Dachun; Madigan, Darold L.; McDaniel, Keith F.; Randolph, John T.; Rockway, Todd W.; Rosenberg, Teresa A.; Stewart, Kent D.; Stoll, Vincent S.; Wagner, Rolf; Yeung, Ming C.; US2005/107364; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

39478-78-9, Adding some certain compound to certain chemical reactions, such as: 39478-78-9, name is 5-Bromo-2-methylaniline, 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 39478-78-9.

General procedure: In a typical run, h-BN(at)Fur(at)Pd(OAc)2 (0.05 mmol) was added to a mixture of arylboronic acid 1 (1.0 mmol), aryl bromide 2 (1.5 mmol) and K2CO3 (1.5 mmol) in water (1 mL). The resulting mixture was stirred at 70 C under Ar protection, and the progress of the reaction was monitored by TLC. After completion of the reaction, ethyl acetate was added to the reaction mixture and the catalyst was separated. The organic phase was washed with water, dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. Finally, the residue was isolated by chromatography on a column of silica gel to afford the corresponding product 3.

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 39478-78-9.

Reference:
Article; Li, Weijian; Lv, Guanghui; Cheng, Xu; Sang, Rui; Ma, Xiaojun; Zhang, Yong; Nie, Ruifang; Li, Jie; Guan, Mei; Wu, Yong; Tetrahedron; vol. 72; 52; (2016); p. 8557 – 8564;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, 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. 3814-30-0

EXAMPLE 136 4-(4-Chloro-3-cyclopentylmethylsulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ole 6.7 g of 4-(4-Chloro-3-sulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ole (Example 2) were introduced, while stirring, into a mixture of 10 ml of absolute dimethyl sulfoxide and 1.2 g of pulverized potassium hydroxide with the exclusion of nitrogen, the temperature being maintained between 8 C and 12 C by outward cooling. While cooling and stirring were maintained, 3.3 g of cyclopentylmethylbromide were added dropwise, the mixture was stirred for 10 hours at room temperature and precipitated with 100 ml of water. The oily residue was decanted, the amorphous product was solidified under 100 ml of fresh water, suction-filtered and washed with water several times. Yellow-brown solid substance, decomposition beginning at 72 C. The IR-spectrum was identical with that of Example 76.

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 3814-30-0.

Reference:
Patent; Hoechst Aktiengesellschaft; US4061761; (1977); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 2695-47-8, name is 6-Bromo-1-hexene, molecular formula is C6H11Br, 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. 2695-47-8

Step A: Preparation of 2,2,2-trifluoro-N-(hex-5-enyl)-N-methylacetamide 1a. At 0 C. and under nitrogen atmosphere, sodium hydride (60% dispersion in mineral oil, 31.5 g, 1.28 eq.) was slowly added to a cooled solution of N-methyl-2,2,2-trifluoroacetamide (100 g, 1.28 eq.) in DMF (500 mL). The reaction mixture was stirred for 2 hrs at 0 C. and 6-bromo-1-hexene (100 g, 1 eq.) was added dropwise for 45 min. The reaction mixture was allowed to warm up to room temperature and was stirred for 3 days. The reaction mixture was poured into water and extracted three times with EtOAc. The combined organic layers were dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The resulting residue was purified by chromatography on silica gel (petroleum ether/EtOAc) to yield compound 1a as colourless oil in 56% yield. 1H NMR (DMSO-d6, 400 MHz) delta (ppm) 1.27-1.38 (m, 2H), 1.48-1.60 (m, 2H), 2-2.06 (m, 2H), 2.93 (m, 3H), 3.35-3.40 (m, 2H), 4.92-5.04 (m, 2H), 5.73-5.83 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2695-47-8, its application will become more common.

Reference:
Patent; Idenix Pharmaceuticals, Inc.; US2010/260710; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

55289-36-6, The chemical industry reduces the impact on the environment during synthesis 55289-36-6, name is 3-Bromo-2-methylaniline, I believe this compound will play a more active role in future production and life.

31 mL of 1N sulfuric acid aqueous solution was added to 3-bromo-2-methylaniline (4.04 g, 21.7 mmol), andthe mixture was cooled to 0C. Sodium nitrite (6.0 M aqueous solution, 4.3 mL) was slowly added thereto. After 15minutes, 10 mL of sulfuric acid was added thereto, and the mixture was stirred for 1 hour under reflux. The reactionsolution was cooled to room temperature. After addition of water, the reaction solution was extracted with Et2O. Theorganic layer was dried with anhydrous magnesium sulfate and purified by column chromatography to obtain the titlecompound (2.34 g, 58 %).1H-NMR (CDCl3) delta 7.14 (1H, d), 6.92 (1H, t), 6.71 (1H, d), 4.83 (1H, brs), 2.34 (3H, s)

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

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

51437-00-4, A common compound: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

1.6 M n-BuLi in hexane (7.94 mL, 12.70 mmol) was added to a solution of bis ( isopropyl ) amine (2.246 mL, 15.87 mmol) in THF(dry) (10 mL) at -78 C. The mixture was stirred at -7.8 C under Ar for 30 min. The solution of 4-bromo-l-fluoro-2- methylbenzene (1.338 mL, 10.58 mmol) in THF was added. The mixture was stirred at -78 C under Ar for 1 h. Propan-2-one (0.935 mL, 12.70 mmol) was added. The mixture was stirred at – 78C under Ar for 2 h. The mixture was poured into IN HC1 aq. and extracted with EtOAc. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 3% – 12% EtOAc in hexane) to give the title (4065) compound (1.780 g, 7.20 mmol, 68.1%) as white solids. (4066) 1H NMR (300 MHz, DMSO-d6) 5:1.-46 (6H, d, J = 1.1 Hz), 2.21 (3H, d, J = 2.6 Hz), 5.39 (1H, s), 7.32-7.42 (1H, m) , 7.55 (1H, dd, J = 6.8, 2.6 Hz) .

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-Bromo-1-fluoro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, Satoshi; SHIRAI, Junya; KONO, Mitsunori; SHIOKAWA, Zenyu; YUKAWA, Tomoya; IMADA, Takashi; NEGORO, Nobuyuki; ODA, Tsuneo; SASAKI, Satoshi; NARA, Yoshi; SUZUKI, Shinkichi; SATO, Ayumu; ISHII, Naoki; SHIBUYA, Akito; NAKAGAWA, Yasuo; COLE, Derek; GIBSON, Tony; IVETAC, Anthony; SWANN, Steve; TYHONAS, John; (472 pag.)WO2018/30550; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 766-81-4, name is 3-Bromophenylacetylene, 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 766-81-4. 766-81-4

To a mixture of bis(triphenylphosphine)palladium(II) dichloride (134 mg, 0.191 mmol), copper(I) iodide (36 mg, 0.191 mmol) and triethylamine (15 mL) in anhydrous tetrahydrofuran (65 mL) under an atmosphere of argon were sequentially added a solution of 6-iodobenzodioxane (5.00 g, 19.08 mmol) in anhydrous tetrahydrofuran (15 mL) and a solution of (3-bromophenyl)acetylene (3.63 g, 20.03 mmol) in anhydrous tetrahydrofuran (10 mL). The resulting solution was stirred at room temperature for 3 days. The crude mixture was diluted with ethyl acetate, washed sequentially with 1 M hydrochloric acid, water and saturated aqueous sodium hydrogen carbonate, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography, using ethyl acetate in heptane (0-15%) as the eluent, gave the title compound in 94% yield: 1H NMR (CDCl3) 5 7.67 (t, J= 1.6 Hz5 1 H), 7.42 – 7.46 (m, 2 H), 7.21 (t, J= 8.0 Hz, 1 H), 7.01 – 7.06 (m, 2 H), 6.84 (d, J= 7.8 Hz, 1 H), 4.26 – 4.31 (m, 4 H); MS (EI) m/z 3U, 316 [M+.].

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 3-Bromophenylacetylene.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2008/76046; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

553-94-6, Name is 2,5-Dimethylbromobenzene, 553-94-6, belongs to bromides-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.

Add 15 mL of solvent dichloromethane to a 100 mL round bottom flask and weigh 3.0 g (16.21 mmol)2,5-Dimethylbromobenzene was added to a round bottom flask containing dichloromethane to make them mutually soluble, put into a stir bar, and stirred under ice water bath; 10 mL of dichloromethane was added to a 100 mL beaker, and 3.240 g was quickly weighed. (24.32 mmol) anhydrous aluminum chloride powder was added to a beaker containing dichloromethane, 2.36 g (27.56 mmol) of acetyl chloride was weighed into a beaker, and stirred with a glass rod to completely dissolve anhydrous aluminum trichloride. After dissolving, it was transferred to a constant pressure funnel, and then slowly and continuously added dropwise to the above 2,5-dimethylbromobenzene solution, and the reaction was stirred under an ice water bath condition; after the dropwise addition, the ice water bath was stirred for 1 hour, and the ice water bath was removed. The reaction was stirred at room temperature for 15 h; after the reaction was over, the burgundy solution obtained by the reaction was slowly added to a beaker containing 300 mL of cold water, and continuously stirred with a glass rod until the solution turned from burgundy to yellowish, and after cooling, Dichloromethane extraction (extraction 2 times, once with 100 mL), the lower layer of methylene chloride was retained, poured into a 500 mL beaker, dried over anhydrous sodium sulfate for 5 h, dried and filtered, and then evaporated. The solvent is removed, and the crude product is added. 100mL round bottom flask was added n-hexaneRecrystallization. The crude product was crystallized to give 2.76 g of white crystals, yield 75%.

Statistics shows that 2,5-Dimethylbromobenzene is playing an increasingly important role. we look forward to future research findings about 553-94-6.

Reference:
Patent; Heilongjiang University; Li Hongfeng; Wang Cheng; Sun Zhiyao; Sun Longjiang; Zheng Rongrong; Ma Dongge; Guo Dechao; Cui Guofeng; Yan Pengfei; (24 pag.)CN109096084; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 202865-83-6

Intermediate 157: 4-Fluoro-2-methyl-benzaldehvde; A solution of 10 g of 5-Bromo-3-fluorotoluene (0.05 mole) in 500 mL of THF was cooled to -780C. Then, 32 mL of a solution of n-Butyl lithium in hexanes (2.5 M, 0.08 mole) were added to the mixture keeping the internal temperature between -75C and -78C. The resulting mixture was stirred at -780C for 50 min. 43 mL of Dry DMF (0.53 mole) were added over 1 h to the mixture. The mixture was allowed to warm to RT (about 180C) and stirred overnight. The reaction was quenched with 20 mL of a saturated solution of NH4CI. The mixture was washed with water (5×100 mL) and the organic layer was washed with a 50 mL of a saturated aqueous solution of NaHCO3, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by a column chromatography on silica gel (PE/AcOEt=50/1 ) to give the title compound as light yellow liquid (3.0Og, 41.09%).

The synthetic route of 202865-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/148853; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

2044-08-8, 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. 2044-08-8, name is 1-Bromocyclohex-1-ene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Add 20 g (0.12 mol) of 1-bromo-1-cyclohexene to a three-necked flask under nitrogen atmosphere.34.7 g (0.14 mol), 2.0 g (6 mol%) of triphenylphosphine,Trans-bis(triphenylphosphine)palladium dichloride (II)2.6 g (3 mol%), potassium phenate 24.6 g (0.19 mol) andAnhydrous toluene 250 mL.After nitrogen substitution, the reaction was stirred at 50 C for 5 hours.The system was then cooled to room temperature and quenched with water.The reaction mixture was extracted with a benzene solvent and brine.The organic phase was dried over anhydrous magnesium sulfate.The dried mixture was filtered and concentrated under reduced pressure.Purified by silica gel column or distillation21.9 g (yield: 85%) cyclohexene-1-boronic acid pinacol ester

The synthetic route of 1-Bromocyclohex-1-ene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yurui (Shanghai) Chemical Co., Ltd.; Zheng Xianzhe; (52 pag.)CN109206456; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary