Bromine → Methy 4-amino-3-bromo-5-[(2-hydroxy-2-methylpropyl)amino]benzoate

Participants

Reaction Steps

To a solution of methy 4-amino-3-[(2-hydroxy-2-methylpropyl)amino]benzoate (1.5 g, 6.30 mmol) in DCM (12.59 mL) added bromine (0.324 mL, 6.30 mmol) drop-wise. The reaction was complete upon total addition of bromine. Reaction mixture was quenched with sodium sulfite and diluted with EtOAc. The aqueous layer was washed with EtOAc (3×). The combined organics were dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% TFA) gave the title compound (0.538 g): LC-MS [M]=317.2.

Provenance & Evidence