6-Bromo-7-fluoroquinoline Chemical Properties

Boiling point:

295.7±20.0 °C(Predicted)

Density 

1.647±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

3.01±0.17(Predicted)

form 

solid

color 

Off White

Safety Information

HS Code 

2933499090

6-Bromo-7-fluoroquinoline Usage And Synthesis

Chemical Properties

Light Yellow Solid

Synthesis

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).

References

[1] Patent: CN105968115, 2016, A. Location in patent: Paragraph 0560-0562
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290
[3] Patent: US2007/265272, 2007, A1. Location in patent: Page/Page column 31-32
[4] Patent: WO2013/144737, 2013, A2. Location in patent: Paragraph 252
[5] Patent: US2015/57309, 2015, A1. Location in patent: Paragraph 0509