ChemicalBook CAS DataBase List 6-Bromo-7-fluoroquinoline

6-Bromo-7-fluoroquinoline synthesis

4synthesis methods

Product Name:6-Bromo-7-fluoroquinoline
CAS Number:127827-52-5
Molecular formula:C9H5BrFN
Molecular Weight:226.05

656-65-5

56-81-5

127827-52-5

General procedure for the synthesis of 6-bromo-7-fluoroquinoline from 4-bromo-3-fluoroaniline and glycerol: Intermediate 2: (7-fluoroquinolin-6-yl)methylamine Step 1: Synthesis of 6-bromo-7-fluoroquinoline: 4-bromo-2-fluoroaniline (10 g, 52.62 mmol), ferrous sulfate (3.33 g, 11.97 mmol) and glycerol (15.78 mL) were mixed. Concentrated sulfuric acid (9.15 mL) was added slowly and the reaction mixture was heated to 140 °C. After 12 hours of reaction, the mixture was cooled to 0 °C and the pH was adjusted to 10-12 with 10% sodium hydroxide solution.The reaction mixture was filtered through diatomaceous earth and washed with ethyl acetate to separate the organic and aqueous layers. The organic layer was washed with brine solution, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by column chromatography (eluent: ethyl acetate/petroleum ether) to give the title compound as a white solid (4.9 g, 44% yield). 1H-NMR (δppm, CDCl3, 400MHz): δ 8.96 (dd, J=4.3,2.7Hz, 1H), 8.15 (m, 2H), 7.81 (d, J=9.5Hz, 1H), 7.42 (dd, J=8.3,4.3Hz, 1H).

656-65-5 Synthesis

656-65-5
314 suppliers
$5.00/1g

56-81-5 Synthesis

56-81-5
1771 suppliers
$5.00/25g

127827-52-5
110 suppliers
$18.00/250mg

Yield: 85.8%

Reaction Conditions:

with sulfuric acid;sodium 3-nitrobenzenesulfonate in water at 120 - 140;

Steps:

1 Synthesis step 1: 7-fluoro-6-bromoquinoline
The starting material, 3-fluoro-4-bromoaniline (20 g, 0.105 mol) And catalyst sodium 3-nitrobenzenesulfonate (28 g, 0.124 mol, 1.2 eq) was added to a mixed solution of concentrated sulfuric acid (60 ml) and water (24 ml), heated to an internal temperature of 120 ° C, Glycerol (29 g, 0.315 mol, 3 eq) was added slowly and the reaction was warmed to 130-140 ° C overnight after the addition was complete and allowed to cool. The reaction solution was poured into crushed ice, concentrated ammonia to pH 8, extracted with dichloromethane, washed with water, After drying, column chromatography purified to give a yellow solid 20.3g, yield 85.8%.

References:

Shanghai Pharmaceutical Group Co., Ltd.;Yu Jianxin;Zhao Fei;Hao Yu;Li Ping;Xia Guangxin;Fan Yi CN105968115, 2016, A Location in patent:Paragraph 0560-0562

367-24-8 Synthesis