Tag: M.W=200-300

Synthetic Route of 103977-79-3, The chemical industry reduces the impact on the environment during synthesis 103977-79-3, name is 3-Bromo-2,4-difluoroaniline, I believe this compound will play a more active role in future production and life.

C. Ethyl 7-bromo-6,8-difluoro-4-hydroxyquinoline-3-carboxylate A stirred mixture of 26 g of 3-amino-2,6-difluorobromobenzene and 27 g of diethyl ethoxymethylenemalonate was heated at 150 C. for 1 hour. After cooling, 100 ml of Dowtherm “A” (commercially available high boiling inert solvent mixture of diphenylether and dibenzofuran) was added and the mixture was heated under nitrogen at 260 C. for 1.5 hour. The mixture was cooled to room temperature and 200 ml of hexanes was added. The resulting precipitate was collected by filtration, washed with hexanes and dried to give a cream solid, m.p. 285 C., yield 78% (32.32 g).

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, 3-Bromo-2,4-difluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US4623650; (1986); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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 1-(3-Bromophenyl)-N,N-dimethylmethanamine

(ii) 3-Bromo-N,N-dimethylbenzylamine (21.4 g) was reacted with magnesium turnings (2.4 g) in dry tetrahydrofuran (75 ml). The mixture was cooled to 0 and gaseous formaldehyde (generated by heating 15 g paraformaldehyde in a stream of argon) was passed over the stirred solution. Tetrahydrofuran (25 ml) was added and the mixture was stirred at room temperature for 2.5 hours and acidified to pH 1. The mixture was extracted with aqueous 3N hydrochloric acid, and the aqueous extracts were made alkaline with aqueous sodium hydroxide and extracted with ether. The ether extracts were evaporated to give 3-(dimethylaminomethyl)benzyl alcohol (14.78 g, 78%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4885-18-1, its application will become more common.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4496567; (1985); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 112734-22-2,Some common heterocyclic compound, 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, molecular formula is C7H7BrFN, 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 1 : N-(4-Bromo-2-fluorobenzyl)-l-phenylmethanesulfonamide To a solution of (4-bromo-2-fluoro-phenyl)methanamine (3 g, 14.7 mmol) in dichloromethane (50 mL) was added N,N-diisopropylethylamine (3.3 mL, 19.1 mmol), followed by phenylmethanesulfonyl chloride (3.3 g, 17.6 mmol) and the reaction was stirred at ambient temperature for 3 hours. The reaction was diluted with dichloromethane and washed with water and brine, dried with MgS04, concentrated and purified by silica gel column chromatography (20-100% EtOAc in heptane) to give N- [(4-bromo-2-fluoro-phenyl)methyl]-l-phenyl-methanesulfonamide (4.22 g, 80% yield). LCMS (m/z) ES+ 358 [M+l]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-Bromo-2-fluorophenyl)methanamine, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FAUBER, Benjamin; RENE, Olivier; WO2013/92941; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 57946-63-1,Some common heterocyclic compound, 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.

A round-bottom flask was charged with 2-bromo-4-(trifluoromethyl)aniline (4.115 g, 17.14 mmol), l-methyl-5-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)-lH- pyrazole (4.64 g, 22.29 mmol), potassium phosphate (10.92 g, 51.4 mmol), and Pd(AmPhos)2Ci2 (0.607 g, 0.857 mmol). Dioxane (30 mL) and water (10 mL) were added to give a thick suspension. The flask was fitted with a reflux condenser and placed in a 90 ¡ãC oil bath for 4 h. The mixture was removed from the heat, then diluted with water and extracted with EtOAc (3x). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The residue was partially purified twice by chromatography on silica gel, first with 25 to 75percent EtO Ac/Heptane, then with 20 to70percent EtO Ac/Heptane. The partially purified material thus obtained was dissolved in methanol and loaded onto a lOg SCX-2 ion exchange column. The column was eluted with methanol, then with 2N ammonia in methanol. The basic fractions were combined and concentrated to give 2-(l-methyl-lH-pyrazol-5-yl)-4-(trifluoromethyl)aniline (0.5526 g, 2.291 mmol, 13.36 percent yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) delta = 7.52 (d, J = 1.9 Hz, 1 H), 7.43 (ddd, J = 0.5, 2.3, 8.6 Hz, 1 H), 7.26 (d, J = 1.9 Hz, 1 H), 6.88 (d, J = 8.5 Hz, 1 H), 6.32 (d, J = 1.9 Hz, 1 H), 5.62 (s, 2 H), 3.64 (s, 3 H). m/z (ESI) 242.2 (M+H)+.

The synthetic route of 57946-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DINEEN, Thomas; MARX, Isaac, E.; NGUYEN, Hanh, Nho; WEISS, Matthew; AMGEN INC.; WO2013/25883; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 18599-22-9, These common heterocyclic compound, 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene, 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.

General procedure: In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, were placed benzoyl chloride (5a, 0.17 mL, 1.5 mmol), Cu2O (0.027 g, 0.18 mmol), 2,2′-bipyridyl (0.019 g, 0.12 mmol), and a DMF solution of 2-Zn (0.61 M, 1.0 mL, 0.61 mmol), and the whole were stirred at room temperature for 20 h. The resultant was poured into water and the organic products were extracted with Et2O three times. The combined organic layers were dried over anhydrous Na2SO4, then filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to give the corresponding 6a (0.13 g, 0.56 mmol) in 92% yield as a colorless oil.

Statistics shows that 4-Bromo-3,3,4,4-tetrafluorobut-1-ene is playing an increasingly important role. we look forward to future research findings about 18599-22-9.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 18599-22-9, A common heterocyclic compound, 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene, molecular formula is C4H3BrF4, 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.

General procedure: In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, were added iodobenzene (3a, 0.40 mL, 3.6 mmol) and Cu2O (0.027 g, 0.18 mmol), and a DMF solution of 2-Zn (0.60 M, 1.0 mL, 0.6 mmol). The whole was heated up at 100 C and stirred at that temperature for 24 h. After cooling to room temperature, the resultant was filtered through a short pad of silica gel using hexane as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography using hexanes as an eluent, leading to the corresponding compound 4a (0.036 g, 0.17 mmol) in 29% isolated yield as a colorless oil.

The synthetic route of 18599-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 156682-52-9,Some common heterocyclic compound, 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, molecular formula is C6H2Br2F2, 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.

Intermediate 4 (5 g, 18.1 mmol),1,4-dibromo-2,3-difluorobenzene (2.4 g, 9.0 mmol), Tetrakis (triphenylphosphine) palladium (0) (0.9 g, 0.9 mmol) Tetrahydrofuran (60 ml) and potassium carbonate 2M solution (20 ml) were added to a mixed solvent and refluxed for 24 hours.After completion of the reaction, the reaction solution was extracted with methylene chloride and methylene chloride / hexane mixed solvent was subjected to column chromatography with a developing solvent to obtain 4.3 g of intermediate 5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Dibromo-2,3-difluorobenzene, its application will become more common.

Reference:
Patent; LG Chem, Ltd.; Dankook University Cheonan Campus Industry-Academic Cooperation Foundation; Gu Gi-dong; Lee Gi-gon; Keum Su-jeong; Kim Gong-gyeom; Lee U-cheol; Lee Chil-won; Cha Jae-ryeong; Joo Yun-seok; (37 pag.)KR2019/109846; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 22034-13-5, name is 4-Bromobenzo[c][1,2,5]thiadiazole, A new synthetic method of this compound is introduced below., Product Details of 22034-13-5

A mixture of 2,7-bis-boronic acid pinacol ester-4-hexylcarbazole-9,9-diarylfluorene (0.2 g, 0.24 mmol, 1 equiv), 4-bromo-2,1,3-thiadiazole (0.206 g, 1 mmol, 4 equiv) were dissolved in 15 ml of a dry bubbling packed with tetrahydrofuran in N2, 5 ml of potassium carbonate aqueous solution (2 mol / L), followed by the addition of 40 mg of palladium catalyst tetraphenylphenylphosphine The reaction mixture was heated at 85 ¡ã C for 24 h and extracted with methylene chloride. After drying, the mixture was purified by rotary distillation using petroleum ether: dichloromethane = 4: 1 silica gel to give a powdery solid in 68percent

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; Nanjing Tech University; Han Yamin; Bai Lubing; Lin Jinyi; (12 pag.)CN106967056; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, A new synthetic method of this compound is introduced below., SDS of cas: 33070-32-5

40 g (0.169 mol) of the 5-bromo-2,2-difluorobenzodioxole prepared in Example 1 and 108 g (121.5 ml) of tetrahydrofuran were placed in a 1 L reaction flask, and the mixture was stirred under a nitrogen atmosphere to cool the system to -10 C, control system temperature -10 ~ 0 C, A solution of 104 g (0.202 mol) of 20% isopropylmagnesium chloride in tetrahydrofuran was added dropwise to the system to control the dropping rate, and the dropwise addition was completed in about 3 hours. After the completion of the dropwise addition, the reaction was kept for 2 hours. The temperature was further lowered to -25 C, and 18.5 g (0.253 mol) of N,N-dimethylformamide was added dropwise, and the mixture was kept for 2 hours. Quenched by adding 200 ml of saturated ammonium chloride solution, adding 15% hydrochloric acid to adjust the pH value of 5-6, adding 250 g of dichloromethane to extract, layering, transfer the lower organic phase to 500 ml reaction flask at 60 C, and concentrate under reduced pressure until no fraction was obtained to give the intermediate product 2,2-difluoro-1,3-benzodioxan-5-carbaldehyde 28.6 g (0.153 mol). The system was cooled to 20-30 C, and 180 g of absolute ethanol was added.Under nitrogen protection, stirring was started, and 2.55 g (0.067 mol) of sodium borohydride was slowly added to the system in portions, and the addition was completed in about 3 hours. After the addition of heat for 30 min, the reaction was quenched by adding 800 g of water, and then extracted with 205 g of dichloromethane, and the mixture was allowed to stand for separation. The lower organic layer was evaporated and concentrated at 60 C, -0.08Mpa (G) to no fraction, and obtain the 2,2-fluorobenzo[d][1,3]dioxo-5-yl)methanol 25.7g, The purity of the gas was determined by gas chromatography to be 96% (0.131 mol, yield 77.7%, based on 5-bromo-2,2-difluorobenzodioxole)

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; Fuxin Da Deli Chemical Co., Ltd.; Nie Qiang; Zhang Jinsheng; Jiang Shan; Jia Yitong; (9 pag.)CN109503544; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, belongs to bromides-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 337915-79-4, COA of Formula: C7H9BrN2

Example 30 4- ( (4-Chlorobenzyl) oxy) -1- (2-isopropyl-l-methyl-lH- benzimidazol-6-yl) pyridin-2 (1H) -one A) 6-Bromo-2-isopropy1-1-methyl-lH-benzimidazole To a solution of 5-bromo-Nx-methylbenzene-l, 2-diamine. (122 mg) and isobutyric acid (0.056 ml) in DMF (2 ml) was added HATU (242 mg) at room temperature. The mixture was stirred at room temperature under a dry atmosphere (CaCl2 tube) for 1 h. After being stirred, N, N-diisopropylethylamine (0.311 ml) was added to the reaction mixture. The mixture was stirred at room temperature for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgS04 and concentrated in vacuo. The resulting residue was stirred in AcOH (2.00 ml) at 90C for 1 h and at room temperature overnight. The mixture was quenched with saturated NaHCC>3 solution at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSC>4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (119 mg) as a pale yellow solid. MS (ESI+) : [M+H]+ 255.0.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KASAI, Shizuo; IGAWA, Hideyuki; TAKAHASHI, Masashi; MAEKAWA, Tsuyoshi; KAKEGAWA, Keiko; YASUMA, Tsuneo; KINA, Asato; AIDA, Jumpei; KHAMRAI, Uttam; KUNDU, Mrinalkanti; WO2013/105676; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary