4-Bromo-5-fluoro-2-nitroaniline

Synthesis

The general procedure for the synthesis of 4-bromo-5-fluoro-2-nitroaniline, using the compound (CAS: 929279-27-6) as starting material, was as follows:Preparation of Intermediate 11B: To (4-bromo-5-fluoro-2-nitrophenyl)-2,2,2-trifluoroacetamide (3.5 g, 10.5 mmol) was added methanol (30 mL), followed by potassium carbonate (1.0 M 10.5 mL, 10.5 mmol). The reaction mixture was stirred for 30 min (Ref. Charifson, PS; et al. J. Med. Chem. 2008, 51, 5243-5263). Upon completion of the reaction, the reaction solution was diluted with deionized water and stirring was continued for 1 hour. The resulting orange solid was collected by filtration and dried in a vacuum oven to give the final target product 4-bromo-5-fluoro-2-nitroaniline (2.1 g, 8.8 mmol, 84% yield).

References

[1] Patent: WO2012/83170, 2012, A1. Location in patent: Page/Page column 154-155
[2] Tetrahedron Letters, 2008, vol. 49, # 44, p. 6348 - 6351
[3] Patent: WO2007/30366, 2007, A1. Location in patent: Page/Page column 121
[4] Patent: US2007/259936, 2007, A1. Location in patent: Page/Page column 175