4-Bromophenol → 1-Bromo-4-(ethenyloxy)benzene

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-bromophenol (75 g, 433.5 mmol), acetic acid ethenyl ester (80.5 mL, 867.0 mmol) and sodium carbonate (27.6 g, 260.10 mmol) in toluene (430 mL) add di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)diiridium (2.9 g, 4.34 mmol) and the heat the mixture at 100° C. for 2.5 hours. Cool the mixture to ambient temperature, dilute with ethyl acetate (EtOAc) (300 mL) and wash once with water (400 mL). Separate the organic portion and wash once with brine (250 mL). Dry the material over sodium sulfate, filter, and concentrate under reduced pressure. Purify the crude mixture by flash chromatography (0% to 5% EtOAc/Hex) to give the title compound (63.5 g, 74%): GCMS: 198.

Provenance & Evidence