Hydrochloric Acid → 4-Amino-2-bromo-3-methylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of commercially available 3-bromo-2-methyl-phenylamine (1.86 g, 10 mmol) in DMSO (200 mL) was added concentrated HCl (10 mL), followed by CuCl2 (2.7 g, 20 mmol). The resulting suspension was heated to 90° C. for 6 h. After cooling to rt, the reaction mixture was poured into ice/water (600 mL) and adjusted to pH=8 by dropwise addition of 10% aqueous NaOH. The resulting greenish suspension was filtered through a pad of Celite®, and the filtrate extracted with ether (3×). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was chromatographed (silica gel), eluting with 30-70% EtOAc/hexane to furnish the title compound (0.67 g, 31%).

Provenance & Evidence