Hydrochloric Acid → 2'-Fluorobiphenyl-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 7.0 g 3-(2-fluorophenyl)-toluene and 29.5 g potassium permanganate in 500 ml t-butanol and 100 ml water was heated at 90° C. for 18 hours. The reaction mixture was cooled to room temperature, sufficient sodium bisulfite was added to dissolve the remaining potassium permanganate and manganese dioxide, and the pH was adjusted to 1 with hydrochloric acid. The resulting precipitate was collected by filtration, redissolved in ethyl acetate and this solution was dried and evaporated yielding the product as a white solid of m.p. 147°-148° C. after recrystallization from hexanes (5.7 g, 70% yield). NMR (DMSO-d6, 250 MHz): 8.2-7.3 (m, 8H).

Provenance & Evidence