Hydrogen Bromide → HCID 89825521, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-fluoro-2-methyl-6-nitroaniline (5.1 g, 30 mmol) in water (38 mL) and aqueous HBr (15 mL, 40%) was refluxed for 10 minutes and then cooled to 0° C. A solution of NaNO2 (2.07 g, 30 mmol) in H2O (12 mL) was added dropwise at a temperature <10° C. The diazonium solution was stirred for 30 minutes at a temperature of 0° C. to 5° C. and was then added slowly to a stirred mixture of CuBr (4.33 g, 30 mmol) in aqueous HBr (12 mL, 40%) and water (23 mL) at RT. The mixture was stirred at RT for 30 minutes and then on a steam bath for 1 hour. The reaction mixture was cooled to RT, DCM (50 mL) was added, and the mixture was washed with saturated NaHCO3 and brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography, eluting with petroleum ether to give the title compound as an oil (2.0 g, 28%). 1H NMR (400 MHz, CDCl3) δ ppm 7.23 (1H, dd, J1=2.4 Hz, J2=7.2 Hz), 7.14 (1H, dd, J1=2.8 Hz, J2=8.8 Hz), 2.44 (3H, s).

Provenance & Evidence