Bromine → 2-(Benzyloxy)-4-bromo-6-methylaniline

Participants

Reaction Steps

A solution of 2-benzyloxy-6-methyl-phenylamine (3.4 g, 16 mmol) in MeOH/AcOH (50 mL/20 mL) is cooled to 0° C. then a solution of Br2 (0.82 mL, 16 mmol) in AcOH (10 mL) is added dropwise. After the addition, the solution is stirred at RT overnight. The solvent is removed under reduced pressure and the residue adjusted to pH>8 with aqueous K2CO3 solution. The suspension is extracted with EtOAc and the combined organic layers are washed with water, brine, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (hexanes/EtOAc=10:1 to 5:1) to give the title compound as a red solid.

Provenance & Evidence