Sodium Hydroxide → 1-(2-Bromophenyl)-2-methylpropan-1-one

Participants

Reaction Steps

To a suspension of [1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one] (2.2 g, 5.19 mmol) in dichloromethane (18 mL) at room temperature under nitrogen was added dropwise a solution of 1-(2-bromophenyl)-2-methylpropan-1-ol of Step A (1.00 g, 4.36 mmol) in dichloromethane (18 mL) over ca. 5 minutes. After 2 hours, additional [1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one] (0.20 g, 0.47 mmol) was added and the reaction mixture stirred at room temperature for 4 days. The reaction mixture was then diluted with diethyl ether (100 mL) and the resulting suspension added to 1.3 M aqueous sodium hydroxide solution (40 mL) with stirring. After 10 minutes the organic phase was separated, washed with 1.3 M sodium hydroxide (40 mL) and water (50 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound (0.89 g, 90%) as a clear, pale yellow oil.

Provenance & Evidence