Month: June 2021

Related Products of 1786-36-3, A common heterocyclic compound, 1786-36-3, name is (2-Bromo-1-fluoroethyl)benzene, molecular formula is C8H8BrF, 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.

Under a nitrogen atmosphere, nickel bromide (4.4 mg, 0.02 mmol),4,4′-dimethyl-2,2′-bipyridine (3.68 mg, 0.02 mmol),Tetrabutylammonium iodide (14.77 mg, 0.04 mmol) manganese powder (43.95 mg, 0.8 mmol),Add solvent NMP (0.5 mL) and stir well. Weigh 4-iodobenzaldehyde (46.40mg, 0.2mmol) in NMP (0.5mL),After dissolution, add (2-bromo-1-fluoroethyl) benzene (60.92 mg, 0.3 mmol) and mix well.The solution was transferred to a sealed tube. After sealing, the reaction was stirred in an oil bath at 80 C for 24 hours.Cool the reaction to room temperature, ether (5mL)Add an equal volume of saturated ammonium chloride solution to the diluted reaction solution.Filter through a diatomaceous sand core funnel, rinse with a small amount of ether, and collect the filtrate.The filtrate was extracted three times with diethyl ether, and the organic phases were combined (add internal standard dodecane,GC-MS determined crude yield). Dry over anhydrous sodium sulfate, filter, and remove the solvent by distillation under reduced pressure.After the residue was separated by silica gel column chromatography, the product was weighed, and the calculated yield was 46%.

The synthetic route of 1786-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan Qing Chemical University; Yang Yi; Luo Gen; Li Youlin; Tong Xia; He Mengmeng; Jiang Yan; Liu Yingle; Shu Yumei; Zheng Yubin; Lu Wenjie; Zhao Yanchuan; (22 pag.)CN110803977; (2020); A;,
Bromide – Wikipedia,
bromide – Wiktionary

1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, 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. Recommanded Product: 3-Bromobicyclo[4.2.0]octa-1,3,5-triene

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (1092.9 mg, 5.97 mmol) THF (4 mL) was added, cooled to -78 C and the flask was evacuated, re-filled with nitrogen. To the mixture was added 3.7 ml of n-BuLi (3.7 ml, 5.97 mmol, 1.6 M in hexane) dropwise with stirring at -78 C for 25 min. 4- (Benzyloxy)-5-bromo-2-methylbenzaldehyde (1.82 g, 5.97 mmol) in THF (6 mL) was then added to the solution and the mixture was kept stirring for 1 h at -78 C. The resulting mixture was quenched with aqueous NH4CI (15 ml), extracted with EtOAc three times (20 ml each time). The combined extracts were washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (40 g, EtOAc/heptane: 0>10%) to yield (4-(benzyloxy)-5-bromo-2- methylphenyl)(bicyclo[4.2.0]octa-1 (6),2,4-trien-3-yl)methanol as a colorless oil. MS (ES) m/z: 431.10 [M+Na]+.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 955959-84-9, 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. 955959-84-9 name is 4-(4-Bromophenyl)dibenzo[b,d]furan, 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.

A solution of dibenzofuran-4-boronic acid (1.0 g, 4.7 mmol) in ethanol (10 ML) was added to a stirred solution of 1- bromo-4-iodobenzene (1.33 g, 4.7 mmol) and tetrakis- (triphenylphosphine) palladium (0) (271 mg, 5 MOLpercent) in toluene (40 mL). 2N sodium carbonate (4.7 mL, 9.4 mmol) was added and the reaction was heated to 90°C (oil bath temp. ) for 2-3 hrs until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (2 x 20 mL). The combined extract was washed with water and brine. The ethereal solution was dried over anhydrous MGS04, filtered and concentrated in vacuo to yield 4- (4-BROMOPHENYL)-DIBENZOFURAN as a yellow solid, which was used immediately without further purification. A solution of 4-FORMYLPHENYLBORONIC acid (0.9 g, 5.64 mmol) in ethanol (10 mL) was added to a stirred solution of the crude 4- (4-BROMOPHENYL)-DIBENZOFURAN (from the previous reaction) in toluene (40 mL). tetrakis- (Triphenylphosphine) palladium (0) (270 mg, 5 molpercent) and 2N sodium carbonate (4.7 mL, 9.4 mmol) were added and the reaction was heated to 100°C (oil bath temp. ) for 2-3 hrs until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The phases were separated, the aqueous phase being further extracted with ethyl acetate (2 x 20 mL). The combined extract was washed with 0.5 N hydrochloric acid, water and brine and then dried over anhydrous MGS04, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 10-20percent ethyl acetate in hexane as eluent, afforded the title compound has a white solid (1.51g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(4-Bromophenyl)dibenzo[b,d]furan, and friends who are interested can also refer to it.

Reference:
Patent; THE INSTITUTE OF PHARMACEUTICAL DISCOVERY, LLC; WO2004/99170; (2004); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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 944718-31-4 as follows. Recommanded Product: 944718-31-4

5-bromo-1-methyl-1H-benzo[d][1,2,3]triazole (302.3 mg, 1.426 mmol),Benzophenone imine (342.5 mg, 1.890 mmol),t-BuONa (274.2 mg, 2.853 mmol),BINAP (87.8mg, 0.141mmol)And Pd2 (dba) 3 (131.4 mg, 0.1435 mmol)Dissolved in 1,4-dioxane (10 mL).The reaction mixture is at 100 ° C,Stir for 6 hours in a nitrogen atmosphere.After the reaction was completed, it was concentrated under reduced pressure.The residue was diluted with water (50 mL).The resulting mixture was taken with DCM and MeOHThe mixed solvent (10/1 (v/v), 80 mL × 3) was extracted.The combined organic phases were dried over anhydrous Na 2 SO 4 and filtered.The filtrate was concentrated under reduced vacuo afforded title crystallThe crude product was used directly in the next step without further purification.

According to the analysis of related databases, 944718-31-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Peng Ju; Li Xiaobo; Zhang Tao; Hu Haiyang; Chen Wuhong; Bai Changlin; Ke Donghua; Chen Peng; (217 pag.)CN109776522; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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 62871-09-4 as follows. Formula: C10H19Br

To a stirred solution of (S)-nicotine (0.52 g, 3.2 mmol) in AcOH (10 ml) was added 10-bromo-dec-1-ene (1.66 g, 7.58 mmol).The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3.The mixture was washed with saturated aqueous NaHCO3, water and brine successively and dried.Evaporation of the solvent followed by titration with ether afforded 0.74 g (61%) of (S)-1-dec-9-enyl-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide (NDNB-9e) as a brown oil. 1H NMR (300 MHz, CDCl3) delta 9.65 (1H, d, J=5.1 Hz), 9.14 (1H, s), 8.41(1H, d, J=8.1 Hz), 8.09 (1H, dd, J=8.1, 5.1 Hz), 5.75 (1H, m), 4.88-5.10 (4H, m), 3.54 (1H, t, J=8.1 Hz), 3.23 (1H, m), 2.45 (2H, m), 2.22 (3H, s), 1.70-2.10 (6H, m), 1.61 (1H, m), 1.10-1.40 (10H, m); 13C NMR (75 MHz, CDCl3) delta 146.46, 144.39, 143.74, 142.97, 139.07, 128.50, 114.33, 67.17, 62.25, 56.92, 40.74, 36.11, 33.93, 32.35, 29.42, 29.24, 29.15, 29.03, 26.35, 23.41.

According to the analysis of related databases, 62871-09-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Crooks, Peter A.; Dwoshin, Linda; Xu, Rui; Ayers, Joshua T.; US2003/225142; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 327-51-5,Some common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-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.

To a solution of l,4-dibromo-2,5-difluorobenzene (12.6 g, 46.3 mmol) in toluene (300 mL) cooled to -78 C was added butyllithium (18.5 mL, 46.3 mmol) at such a rate that the internal temperature did not exceed -50 C and the reaction was stirred for 45 minutes. To the reaction was added N, N-dimethylacetamide (4.84 g, 55.6 mmol). The reaction was stirred at -78 C and then warmed to ambient temperature over a period of 4 hours. The reaction was quenched by adding water (300 mL) followed by the addition of EtOAc (500 mL) and the layers were separated. The organic layer was washed with brine (100 mL), dried over MgS04, filtered and concentrated in vacuo. The crude material was chromatographed eluting with 10% EtOAc/Hexane to give l-(4-bromo-2,5- difluorophenyl)ethanone (5 g, 21.3 mmol, 45.9 % yield).

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-2,5-difluorobenzene, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; FELL, Jay Bradford; FISCHER, John P.; HINKLIN, Ronald J.; WO2013/74641; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 553-94-6,Some common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, molecular formula is C8H9Br, 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: A round bottom flask was charged with the aryl halide (0.5mmol), phenylboronic acid (0.75mmol), base (1.5 or 3mmol), catalyst (0.01mmol) and solvent (7mL), although the amount of the reagents and catalysts was diminished to half when catalysts 2-4 were utilized. The mixtures were heated for the times 2, 4, 8 and 24h and at the temperatures 85 and 100C given in the tables using the bases and catalysts there indicated. The products were characterized by GC.

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

Reference:
Article; Karami, Kazem; Rahimi, Nasser; Rizzoli, Corrado; Polyhedron; vol. 59; (2013); p. 133 – 137;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1435-51-4, These common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, 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 mixture of tris(dibenzylideneacetone)dipalladium (0.20 g, 0.22 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphine)xanthene (0.13, 0.22 mmol) and cesium carbonate (5.0 g, 15.41 mmol) under N2 gas was added acetamide (0.90, 14.73 mmol), l,3-dibromo-5- fluorobenzene (2.8 g, 10.83 mmol) and dioxane (22 mL). The reaction mixture was heated at 8O0C overnight and concentrated under reduced pressure. Purification by flash chromatography (silica, 50:50 ethyl acetate/hexane) gave N-(3-bromo-5-fluorophenyl)acetamide (3.51 g, quantitative). Retention time (min) = 1.945, method [4], MS(ESI) 232.0 (M+Eta).

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; SHAM, Hing, L.; KONRADI, Andrei, W.; HOM, Roy, K.; PROBST, Gary, D.; BOWERS, Simeon; TRUONG, Anh; NEITZ, R., Jeffrey; SEALY, Jennifer; TOTH, Gergely; WO2010/91310; (2010); A1;,
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. 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, A new synthetic method of this compound is introduced below., Quality Control of (4-Bromo-2-fluorophenyl)methanamine

At 0C, p-toluenesulfonyl chloride (4.00g, 21mmol) was added in portion to a solution of 5-bromo-2-fluorobenzlamine (4.08g, 20mmol) and triethylamine (4.04g, 40mmol) in DCM (60mL). The mixture was reacted at 0C for 30mins, followed by removing the ice bath, further reacting at room temperature for 16hrs, then being concentrated under reduced pressure. The residue was purified by silica column chromatography (PE:EA = 5:1) to give compound 9-f (5.30g, yield 74%). LC-MS (ESI): m/z = 358 [M+H]+.

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; Shanghai Yingli Pharmaceutical Co. Ltd.; XU, Zusheng; ZHANG, Nong; SUN, Qingrui; WU, Tianzhi; (104 pag.)EP3275867; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 14659-58-6, 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. 14659-58-6 name is 2-Bromo-5-fluoro-1,3-dimethylbenzene, 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.

In Step 2, Compound 78 (10 g) was converted Compound 79 using methyl 2- mercaptoacetate in piperidine/pyridine at 100 C. The reaction was stirred for 4 hour prior to purification that yielded Compound 79 (11.7 g). In Step 3, Compound 79 (2 g) was converted to benzothiophene Compound 72 using SOCI2 in xylenes/pyridine. The reaction was heated to 120 C and allowed to stir overnight. In Step 4, Compound 72 is subjected to n-butyl lithium and 2- bromo-5-fluoro-1,3-dimethylbenzene to afford Compound 73. In Step 5, Compound 73 is demethylated using BBr3 to afford Compound 74. In Step 6, Compound 74 is reacted with sodium hydride and benzyl bromide to afford Compound 75. In Step 7, Compound 75 is mixed with Compound 38 and cesium carbonate in DMSO to afford Compound 76. In Step 8, the benzyl protecting group of Compound 76 is removed by hydrogenation to afford Compound 112.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-fluoro-1,3-dimethylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; G1 THERAPEUTICS, INC.; STRUM, Jay, Copeland; (187 pag.)WO2020/37251; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary