Boron tribromide → HCID 19101398, compound

Participants

Reaction Steps

A 1M solution of boron tribromide (17 mL, 0.017 mol) in dichloromethane was added to an ice-cooled solution of methyl 3,5-dibromo-4-(3-isopropyl-4-methoxyphenylsulfonyl)phenylacetate (3.5 g, 0.0067 mol), from Example 1, in dichloromethane. The mixture was warmed to room temperature and allowed to react for 3 hrs. Excess boron tribromide was quenched by the addition of methanol to the ice-cooled reaction mixture and the reaction mixture was concentrated on a rotary evaporator. The residue was dissolved in ethyl acetate, washed with water and brine, and dried (Na2SO4). The residue obtained after removal of the solvent was purified by flash chromatography (silica gel, 45:45:10 hexane:CH2Cl2 : acetone) to obtain methyl 3,5-dibromo-4-(4-hydroxy-3-isopropylphenylsulfonyl)phenylacetate (2.9 g, 0.0057 mol, 85% yield). MP: 159°-160° C. (hexane/ethyl acetate).

Provenance & Evidence