Water → 2-Bromo-4-fluoro-6-nitroaniline

Participants

Reaction Steps

To a mixture of 4-fluoro-2-nitroaniline (10.0 g, 42.55 mmol) in DCM (150 mL) and HOAc (75 mL) at 0° C. was added dropwise Br2 (9.9 ml, 130 mmol) at a rate to maintain the internal reaction temperature below 10° C. The reaction mixture was stirred at RT overnight and then poured into water (500 mL), followed by separation of the organic phase. The pH of the aqueous phase was adjusted to about 7 by adding NH4OH, and the mixture was extracted with DCM (100 mL×3). The combined extracts were dried (MgSO4), filtered, and concentrated in vacuo to afford 2-bromo-4-fluoro-6-nitroaniline as a yellow solid (14 g, 93%). MS (ESI): m/z=233 [M−1]−.

Provenance & Evidence