Water → 3-Bromo-2-fluoro-5-nitrobenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 2-amino-5-bromo-6-fluoro-3-nitro-benzonitrile (8.0 g, 30.8 mmol) in tetrahydrofuran (40 mL) was added tert-butyl nitrite (4.6 mL, 37 mmol) dropwise and stirred for 16 h at 50° C. The reaction mixture was treated with water and extracted with ethyl acetate. The organic fraction was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (2% to 10% ethyl acetate:hexanes) afforded 4.0 g (53%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.72 (dd, J=3.0, 2.7 Hz, 1H), 8.51 (dd, J=3.0, 2.7 Hz, 1H).

Provenance & Evidence