Category: bromides-buliding-blocks

Synthetic Route of 61613-22-7,Some common heterocyclic compound, 61613-22-7, name is 2-Bromo-N-phenylaniline, molecular formula is C12H10BrN, 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.

10 g (42 mmol) of 2-bromo-N-phenylaniline and 150 ml of tetrahydrofuran were added to a reaction container, and the mixture was cooled to -78?C using dry ice. After 3.323 g (52 mmol) of n-butyllithium was slowly dropwise added thereto, the resulting solution was stirred for 1 hour. 17.6 g (52 mmol) of bis(4-bromophenyl)methanone was dissolved in 50 ml of tetrahydrofuran, and slowly dropwise added to the reaction container. After the reaction was completed, the solvent was evaporated and the resulting residue was thoroughly dried. 100 ml of acetic acid:hydrochloric acid (1:10 volume by volume (v/v)) was added thereto, thereby obtaining 15.2 g (yield: 77%) of Intermediate I-4-1.

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

Reference:
Patent; Samsung Electronics Co., Ltd.; Samsung SDI Co., Ltd.; JEON, Soonok; KIM, Sangmo; KIM, Hyungjun; CHUNG, Yeonsook; JUNG, Yongsik; CHAE, Miyoung; HUH, Dalho; KIM, Joonghyuk; IHN, Sooghang; (87 pag.)US2017/5275; (2017); A1;,
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These common heterocyclic compound, 1073-06-9, name is 1-Bromo-3-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. Recommanded Product: 1-Bromo-3-fluorobenzene

Charge an oven-dried 250 mL round-bottom flask with 6-methoxy-1-tetralone (3. 0g, 17.0 mmol. ) and place under nitrogen. Dissolve the solid in toluene (30mL) and add 1-bromo-3-fluorobenzene (4. 7 mL, 42.6 mmol), sodium t-butoxide (6.5g, 68.1 mmol), palladium acetate (76mg, 0.34 mmol), and racemic BINAP (212mg, 0.34 mmol). Heat the solution to 115C and stir for 18 hours. Dilute the solution with cold 5N HC1 (50mL) and ethyl acetate (200mL). Separate the organic layer and dry over sodium sulfate, filter over a pad of celite and concentrate in vacuo. Purify the crude product using radial chromatography to give 3.4 g (74%) of the title compound. This material is used without further purification: mass spectrum (ion spray) m/z =267 (M-H). Dissolve 2- (3-fluoro-phenyl)-6-methoxy-naphthalen-l-ol (3.36g, 12.5 mmol) in N-methyl-2-pyrrolidinone (NMP) (lOmL) and add sodium hydride (500mg, 60% oil dispersion, 12.5 mmol) at room temperature. After stirring for 1 hour this solution is added to a solution of 4-fluorobenzaldehyde (2.4mL, 22.5 mmol) in NMP (lOmL) that has been heated to 185C. Continue stirring for 2.5 hours. Cool the reaction to room temperature and add pH 7 buffer (50mL) and extract with ethyl acetate (2 X 100mL). Wash the organic extracts with water and filter through a plug of silica gel. Purify the crude product using radial chromatography giving 2. 50g (54%) of the title compound and use without further purification: mass spectrum (ion spray) m/z = 371 (M-H). Charge a 100 mL round-bottom flask with 4- [2- (3-fluoro-phenyl)-6-methoxy- naphthalen-l-yloxy]-benzaldehyde (2. 5g, 6.71 mmol) and ethyl acetate (5 mL). At room temperature add 2 mL of 35% hydrogen peroxide. To this solution slowly add 2 mL of concentrated sulfuric acid. The mixture warms to approximately 40 C and returns to room temperature where it is stirred for 2 hours. Dilute the reaction with water and ethyl acetate (100 mL) and dry the organic layer over sodium sulfate, filter and concentrate in vacuo. Purify the crude product using radial chromatography eluting with CH2C12 to yield 540 mg (22%) of the title compound: mass spectrum (ion spray) m/z = 359 (M-H).

The synthetic route of 1-Bromo-3-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/73204; (2005); A1;,
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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. 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H12BrN

General procedure: To a stirred solution of 10 (1.00g, 4.00mmol) and K2CO3 (1.66g, 12.00mmol) in acetonitrile (20mL) was added dropwise diethylamine solution (1.20g, 16.00mmol) at room temperature for 2h. The solvent was evaporated in vacuo and the residue was then dissolved in EtOAc (50mL) and washed with water (20mL×3), the organic layers were washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to provide the 11a (0.83g, 84.7% yield) as an off-white liquid. (0041) Then, a mixture of 11a (0.83g, 3.43mmol), bis(pinacolato)diboron (0.96g, 3.77mmol), PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol) and potassium acetate (0.67g, 6.86mmol) in anhydrous 1,4-dioxane (15mL) was purged with argon and heated at 100C for 2.5h. The reaction was then treated with 6 (1.20g, 3.60mmol), 2.0M aqueous Na2CO3 (5mL) and another portion of PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol), then heated at 110C for 12h under argon. The reaction mixture was cooled to room temperature, filtered, and concentrated. The final compound was purified by MPLC (ISCO CombiFlash purification system) (MeOH/DCM, eluted from 0% to 10%), The fractions were collected, concentrated to afford 12a (0.72g, 57.2% yield).

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:
Article; Han, Jinsong; Chen, Ying; Yang, Chao; Liu, Ting; Wang, Mingping; Xu, Haojie; Zhang, Ling; Zheng, Canhui; Song, Yunlong; Zhu, Ju; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 684 – 701;,
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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. 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 556-96-7

General procedure: In an oven dried round bottomed flask a mixture containing styrene (2.5mmol), aryl halide (2.5mmol), the palladium complex [Pd(OL1)]4 (0.005mmol) and potassium carbonate (10.0mmol) in methanol (10cm3) was heated to reflux for 4h, as mentioned in Table 3. After the reaction was completed, the solvent was evaporated and the reaction mixture was extracted with diethyl ether. The ether solution was dried over Na2SO4 and filtered. The ether solution, containing the reaction mixture, was passed through a 12.48cm silica column (60-120 mesh), the complex was not separated out and it remained trapped in the column. After he desired compound was extracted from the column, the complex was eluted using dichloromethane. Upon evaporation of the ether, solids of the pure products were obtained. The yields of the products obtained from all the reactions were determined after isolation, and the products were characterized by 1H NMR spectra.

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 556-96-7.

Reference:
Article; Pattanayak, Poulami; Pratihar, Jahar Lal; Patra, Debprasad; Lin, Chia-Her; Chattopadhyay, Surajit; Polyhedron; vol. 63; (2013); p. 133 – 138;,
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Synthetic Route of 766-46-1, These common heterocyclic compound, 766-46-1, name is 2′-Bromophenylacetylene, 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: To a solution of sulfonyl azides 1 (0.6 mmol), o-bromo-phenylacetylenes 2 (0.5 mmol), aromatic amines 3 (0.55 mmol), and CuI (0.05 mmol) in DMSO (2 mL) in Schlenk tube was added TEA (0.5 mmol) slowly via a syringe. The reaction solution was stirred at room temperature under N2 for 2 h. The solution was then added to CuI (0.05 mmol), K2CO3 (1 mmol), and l-proline (0.2 mmol), and the mixture was stirred at 60 C under N2 for 4 h. The reaction mixture was partitioned between ethyl acetate and saturated aq NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with petroleum ether and ethyl acetate (6:1 to 9:1).

Statistics shows that 2′-Bromophenylacetylene is playing an increasingly important role. we look forward to future research findings about 766-46-1.

Reference:
Article; Jin, Hongwei; Zhou, Bingwei; Wu, Zhi; Shen, Yang; Wang, Yanguang; Tetrahedron; vol. 67; 6; (2011); p. 1178 – 1182;,
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These common heterocyclic compound, 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, 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. Safety of 4-(4-Bromophenyl)dibenzo[b,d]furan

Under an argon atmosphere, the intermediate body 3H-1 (2.36 g, 7.3 mmol), an intermediate body 3H-2 (3.0 g, 7.3 mmol), CuI (1.4 g, 7.3 mmol), tripotassium phosphate (2.3 g, 11 mmol), anhydrous dioxane (30 mL), and cyclohexanediamine (0.84 g, 7.3 mmol) were loaded in the stated order into a three-necked flask, and were then stirred at 100 C. for 8 hours. Water was added to the reaction liquid to precipitate a solid, and then the solid was washed with hexane and then with methanol. Further, the resultant solid was purified by silica gel column chromatography. Thus, a compound 3H (2.9 g, 60% yield) was obtained. The result of FD-MS analysis confirmed that the compound had a ratio m/e of 650 with respect to its molecular weight, i.e., 650.

The synthetic route of 4-(4-Bromophenyl)dibenzo[b,d]furan has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN CO. LTD.; UNIVERSAL DISPLAY CORPORATION; Yamamoto, Hitoshi; Weaver, Michael S.; Brown, Julia J.; Nishimura, Kazuki; Iwakuma, Toshihiro; (76 pag.)US9966541; (2018); B2;,
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Synthetic Route of 627871-16-3,Some common heterocyclic compound, 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, 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.

Under a nitrogen atmosphere, 5-bromo-4-fluoro-2-methylaniline (2.0 g, 9.80 mmol),Bis (pinacolato) diboron (3.73 g, 14.7 mmol),Palladium acetate (220 mg, 0.98 mmol),X-Phos (701 mg, 1.47 mmoll) and potassium acetate (2.89 g, 29.4 mmol) were suspended in 1,4-dioxane (20 mL),Under heating reflux,Stir for 1.5 hours.It was allowed to cool, diluted with water, and extracted with ethyl acetate.Wash the organic layer with saturated saline,Dried over anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure.The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate),Compound 14(1.65g,Yield 67.0%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-4-fluoro-2-methylaniline, its application will become more common.

Reference:
Patent; Shionogi Co Ltd; Ogawa, Tomoyuki; (39 pag.)JP2019/182806; (2019); A;,
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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. 18599-22-9, name is 4-Bromo-3,3,4,4-tetrafluorobut-1-ene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Bromo-3,3,4,4-tetrafluorobut-1-ene

Under an argon atmosphere, methyl lithium-diethyl ether solution (1.0 M, 2.2 mL) without containing lithium bromide was dropped to tetrahydrofuran solution (2.0 mL) of 4-bromo-3,3,4,4-tetrafluoro-1-butene (0.23 g, 1.1 mmol) and 4- (trans-4-propylcyclohexyl) benzaldehyde (0.55 g, 2.4 mmol) at -78 C and stirred for 2 hours. After that, saturated ammonium chloride aqueous solution was poured into the reaction solution and reaction was stopped. The reaction solution was extracted three times with ethyl acetate, the obtained organic layer was dried with anhydrous sodium sulfate. After drying, filtration was carried out, and the obtained filtrate was concentrated with rotary evaporator. After that, the residue was purified by silica gel column chromatography (hexane / ethyl acetate = 7/1), compound (9-B) was obtained. (0.32 g, 0.88 mmol, 81% yield)

According to the analysis of related databases, 18599-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AGC Seimi Chemical Co., Ltd.; Konno, Tsutomu; Ishihara, Takashi; Asai, Tomoyuki; (24 pag.)JP2016/84300; (2016); A;,
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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. 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-4-fluoro-2-methylaniline

Reference Example 52a; Pyridine (1.0 mL) and acetyl chloride (0.67 mL) were sequentially added to a methylene chloride (17 mL) solution of 5-bromo-4-fluoro-2-methylaniline (1.74 g), followed by stirring at room temperature for 1 hour. Water, 1 mol/L hydrochloric acid, and chloroform were added to the reaction mixture. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Hexane was added to the obtained residue, and the solid substance was collected by filtration to obtain 1.83 g of N-(5-bromo-4-fluoro-2-methylphenyl)acetamide as a white solid.1H-NMR (DMSO-d6) delta: 2.06 (3H, s), 2.18 (3H, s), 7.27 (1H, d, J=9.5 Hz), 7.74 (1H, d, J=6.8 Hz), 9.38 (1H, s).

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; Toyama Chemical Co., Ltd.; US2011/275797; (2011); A1;,
Bromide – Wikipedia,
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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. 771583-12-1, name is 2-(Aminomethyl)-4-bromoaniline, A new synthetic method of this compound is introduced below., Quality Control of 2-(Aminomethyl)-4-bromoaniline

In the 1000 ml three-necked bottle,5 g of 5-bromo-2-aminobenzylamine (molecular weight 200, 0.025 mol) was added, Add 150 ml of methylene chloride, stir, dissolve,Add 11 ml of triethylamine and cool to 0 C. Cooling and stirring, A solution of 20 ml of 4.75 g of beta-naphthoyl chloride dissolved in dichloromethane (molecular weight 190,0.025 moles) was slowly added. Natural to room temperature, stirring for 3 hours.Add 40 ml of water, separate the organic phase, evaporated,To obtain a solid intermediate product. The solid was dissolved in 60 ml of toluene,Add 4 ml of thionyl chloride, reflux for three days, cooling, product precipitation,Add 50 ml of concentrated aqueous ammonia, stir, and filter out 8.4 g of solid dihydro compound.The solid dihydro was dissolved in 80 ml of dichloromethane,Adding 2.3 g of manganese dioxide and stirring at room temperature for 18 hours to filter out the inorganic matter,The organic layer was evaporated to dryness and recrystallized to give 5.35 g of 6-bromo-2- (naphthalen-2-yl) quinazoline with a molecular weight of 334 in 64% yield.

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; Beijing Dingcai Technology Co., Ltd.; Gu’an Dingcai Technology Co., Ltd.; Fan Hongtao; Li Yinkui; Shao Shuang; Ren Xueyan; (35 pag.)CN106554319; (2017); A;,
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