Boron tribromide → HCID 68556350, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [[4-(3-sec-Butyl-4-methoxy-phenoxy)-3,5-dichloro-phenyl]-(4-methoxy-phenoxycarbonyl)-amino]-acetic acid ethyl ester (6.4 g, 0.01 mol) in CH2Cl2 (128 mL) was cooled to −60° C. under nitrogen atmosphere. To that 1M BBr3 (boron tribromide) solution (44.44 mL) was added dropwise. The reaction mixture was allowed to warm up to 20-25° C. over 5 h. then diluted with more CH2Cl2 (30 mL) and quenched with H2O. After stirring at 20-25° C. for 30 min, organic phase was separated, washed with H2O, brine & dried over sodium sulphate, filtered and concentrated to give crude product. The crude product was purified by column chromatography over flash silica gel (chloroform:methanol) gradient elution from 95:5 to 90:10 to give pure [[4-(3-sec-Butyl-4-hydroxy-phenoxy)-3,5-dichloro-phenyl]-(4-hydroxy-phenoxycarbonyl)-amino]-acetic acid (3.3 g, 58% yield)

Provenance & Evidence