Methanol → 3-(3-Bromophenyl)pentanedial

Participants

Reaction Conditions

Reaction Steps

Ozone was bubbled through a solution of 1-bromo-3-(hepta-1,6-dien-4-yl)benzene (6.14 g, 24.4 mmol) in CH3OH (10 ml) and CH2Cl2 (90 ml) at −78° C. for 30 min at which time the solution was pale blue. Nitrogen was then bubbled through the solution for 5 min and the solution became clear. Polymer support triphenylphosphine (20 g, 60.0 mmol) was added and the solution stirred at −78° C. for 30 min. The dry ice/acetone bath was removed and the heterogeneous mixture was stirred for 1 h. The heterogeneous mixture was filtered through Celite and the filtrate was concentrated to afford compound 87.

Provenance & Evidence