3-Amino-4-chlorophenol → N-(2-chloro-5-hydroxyphenyl)-2-(4-methanesulfonylbenzyl)-3-oxo-butyramide

Participants

Reaction Steps

Silver trifluoroacetate (1.3 g) was added in two portions over 20 minutes to a stirred solution of 3-amino-4-chlorophenol (0.5 g) and 2-(4-methanesulfonylbenzyl)-3-oxothiobutyric acid S-tert-butyl ester (0.8 g) in 1,2-dimethoxyethane (10 mL) at room temperature. The mixture was stirred at room temperature for 15 hours and then filtered through hyflo, washing with 1,2-dimethoxyethane. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 0:1 by volume) gave title compound as a pale peach solid, 0.75 g.

Provenance & Evidence