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

Participants

Reaction Conditions

Reaction Steps

Under nitrogen, a 250 milliliter round bottom flask was charged with 4-bromophenol (8.00 grams, 46.2 millimoles, 1.0 equivalent), sodium acetate (2.28 grams, 27.7 millimoles, 0.6 equivalent) and bis(1,5-cyclooctadiene)diiridium(I)dichloride (233 milligram, 347 micromoles, 0.0075 equivalent). Toluene (75 milliliter) was added to this and vinyl acetate (8.5 milliliter, 92 millimoles, 2.0 equivalents) was added via syringe. The reaction was heated to 102° C. for 3 hours and then allowed to cool to room temperature. The crude reaction was concentrated on a rotary evaporator and filtered through a plug of silica. The solvent was removed by rotary evaporation and the product dried under high vacuum. The final compound was obtained in form of a colorless to slightly yellow oil (6.97 gram, 35.0 millimoles, 76%). 1H NMR (500 MHz, CDCl3) δ 7.44-7.37 (m, 2H), 6.91-6.84 (m, 2H), 6.56 (dd, J=13.7, 6.1 Hz, 1H), 4.77 (dd, J=13.7, 1.8 Hz, 1H), 4.45 (dd, J=6.1, 1.8 Hz, 1H).

Provenance & Evidence