3-Chloro-2,5-dimethylaniline → 4-Bromo-3-chloro-2,5-dimethylaniline

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 21B (1.56 g, 10 mmol) in CHCl3 (30 mL) cooled to 0-5° C. was added portionwise tetrabutylammonium tribromide (434 mg, 9.0 mmol). After addition, the reaction was stirred at 0-5° C. for 5 min, then quenched with saturated aqueous NaHCO3 (30 mL) and 5% aqueous Na2S2O3 (30 mL). The mixture was stirred at rt for 10 min, then extracted with CH2Cl2 (3×). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was chromatographed (silica gel), eluting with 20-60% EtOAc/hexane to give the title compound (0.75 g, 32% yield).

Provenance & Evidence