Boron tribromide → HCID 68554902, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of {[4-(3-sec-Butyl-4-methoxy-phenoxy)-3,5-dichloro-phenyl]-ethoxycarbonylmethyl-amino}-acetic acid ethyl ester (12.5 g, 0.02 mol) in CH2Cl2 (250 mL) was cooled to −60° C. under nitrogen atmosphere. To that 1M BBr3 solution (122 mL) was added dropwise. The reaction mixture was allowed to warm up to 20-25° C. over 5 h. then diluted with more CH2Cl2 (250 mL) and quenched with H2O. After stirring at 20-25° C. for 30 min, organic phase was separated, washed with water, 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]-carboxymethyl-amino}-acetic acid (6.8 g, 63% yield)

Provenance & Evidence