Toluene → HCID 19703126, compound

Participants

Reaction Steps

A solution of 4-bromobenzeneboronic acid (2.0 g) in ethanol (10 ml) was added over a period of 15 minutes to a stirred mixture of 6-iodo-2-picolin-5-ol (2.35 g), saturated aqueous sodium carbonate solution (5.0 ml), tetrakis(triphenylphosphine)palladium [0] (280 mg) and toluene (10 ml) under an atmosphere of argon. The mixture was stirred at reflux for 6 hours. The mixture was evaporated and the residue was treated with water (20 ml). The mixture was filtered and the yellow solid collected was purified by flash column chromatography on alumina (1CN Biomedicals Alumina N32-63) using 50% n-pentane/ethyl. acetate as eluent to give 2-(4-bromophenyl)-3-hydroxy-6-methylpyridine (600 mg), m.p. 196°-199° C.; NMR: 2.42(3H,s), 7.09(1H,d), 7.25(1H,d), 7.62(2H,d), 8.02(2H,d), 9.98(1H,s); m/z 264 & 266 (M+H).

Provenance & Evidence