Chemical Properties
Light yellow liquid
Uses
2-Bromo-3-fluoroaniline is used as pharmaceutical intermediate.
Synthesis
General procedure for the synthesis of 2-bromo-3-fluoroaniline from 2-bromo-3-fluoro nitrobenzene: 2-bromo-1-fluoro-3-nitrobenzene (1.0 g, 5.0 mmol) was dissolved in methanol (50 mL) at 0 °C, and NiCl (2.2 g, 10 mmol) and NaBH (0.50 g, 14 mmol) were added sequentially. After the addition was completed, the reaction mixture was stirred at 0 °C for 5 min. Subsequently, the reaction was quenched by the addition of water (20 mL) and extracted with ethyl acetate (20 mL x 3). The organic layers were combined, dried over anhydrous NaSO and concentrated under reduced pressure to afford 2-bromo-3-fluoroaniline (600 mg, 70% yield). The product was characterized by 1H NMR (400 MHz, CDCl): δ 7.07-7.02 (m, 1H), 6.55-6.49 (m, 1H), 4.22 (br s, 2H).
References
[1] Patent: CN108002976, 2018, A. Location in patent: Paragraph 0045; 0047; 0050; 0051; 0060; 0069
[2] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437
[3] Patent: US2007/244159, 2007, A1. Location in patent: Page/Page column 121
[4] Patent: US2011/98311, 2011, A1
[5] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 1674
