Dichloromethane → 2-(4-tert-Butylphenoxy)-N-{3-hydroxy-4-[(methylsulfonyl)amino]benzyl}acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-tert-butylphenoxy)-N-{3-methoxy-4-[(methylsulfonyl)amino]benzyl}acetamide (Example 11) (446 mg, 1.06 mmol) in methylene dichrolide (20 ml) was added 1.0 M methylene dichloride solution of boron(III)bromide (5.3 ml, 5.3 mmol) at 0° C. After being stirred for 1.5 hours at 0° C., the mixture was quenched with water and crude residue was extracted with methylene dichloride. The organic layer was separated, then washed with brine, dried over magnesium sulfate. Then, filtration to remove magnesium sulfate, evaporation under removed pressure gave the residue, which was applied to a silica gel chromatography column and eluted with a volume mixture of hexane : ethyl acetate (2/3) to furnish 293 mg (55% yield) of the title compound as a white solid.

Provenance & Evidence