4-Bromophenol → 3-Methyl-but-2-enoic acid 4-bromo-phenyl ester

Participants

Reaction Conditions

Reaction Steps

To an ice bath cooled solution of 1.66 g (69.2 mmol) of NaH (60% suspension in mineral oil) in 25 ml of dry THF was added slowly under argon a solution of 10.0 g (57.8 mmol) of 4-bromophenol in 50 ml of dry THF. The mixture was stirred at 0 degrees C. for 30 minutes and then treated with a solution of 6.85 g (6.44 ml, 57.8 mmol) of dimethylacryloyl chloride in 25 ml of dry THF. The cooling bath was then removed and the mixture allowed to warm to room temperature. The organic layer was separated and the aqueous layer was washed with 2×25 ml of ether. The combined organic layers were washed with 2×50 ml of water, brine and dried (MgSO4). The solvent was removed in-vacuo and the residue purified using flash chromatography (SiO2 ; 5% ethyl acetate in hexanes) to give the title compound as a pale yellow oil.

Provenance & Evidence