Boron tribromide → 2-{4-[2-(3,4-Dihydroxy-phenyl)-ethyl]-phenylamino}-benzoic acid

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Reaction Steps

To a solution of 2-{4-[2-(3,4-dimethoxy-phenyl)-ethyl]phenylamino}-benzoic acid (0.28 g, 0.74 mmol) in CH2Cl2 (20 mL), BBr3 (3.5 mL, 1M in CH2Cl2, 3.5 mmol) was added at room temperature under a N2 atmosphere. The reaction mixture was allowed to stir at room temperature for 2 hours and then poured into ice water (50 mL). This mixture was extracted with EtOAc, and the organic layer was washed two times with water, dried (Na2SO4), filtered and concentrated in vacuo to yield 0.24 g (0.69 mmol, 93%) of the desired product. mp 215-217° C.

Provenance & Evidence