Water → 1-Bromo-3-fluoro-5-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

Mix water (60mL), concentrated sulfuric acid (60mL) and 4-fluoro-2-nitro-6-bromoaniline (9.65g, 41mmol). Cool to 0° C. and add solid sodium nitrite (4.25g, 61mmol) in small portions at such a rate as not to exceed 5° C. Stir for 30 minutes and add ferrous sulfate heptahydrate (5.6g, 20.5mmol) and ethanol (18mL). Stir with warming to room temperature over 2 hours. Add water (200mL), separate the organic phase and wash the aqueous phase with methylene chloride (2×). Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (5% ethyl acetate/hexane) give 3-bromo-5-fluoronitrobenzene (4.5g); bp 65°-70° [email protected] Hg.

Provenance & Evidence