Chloride → HCID 77231543, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-aminophenylboronic acid pinacol ester (5.04 g, 23.0 mmol) in dichloromethane (100 mL) was added TEA (6.41 mL, 46.0 mmol). The resulting solution was cooled to 0° C., then methacrolyl chloride (2.70 mL, 27.6 mmol) was added. The cooling bath was removed, and the reaction was allowed to warm to room temperature and stir for approximately 2 hours. The reaction mixture was washed with 7.5% aqueous ammonium chloride (100 mL) and the layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford a solid. The solid was triturated with hexanes (50 mL) and isolated by filtration to afford N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methacrylamide. LRMS (ESI) calcd for C16H22BNO3 [M+H]+: 288, found 288.

Provenance & Evidence