(2,4-Dichlorophenyl)boronic acid → 1-(2,4-Dichlorophenyl)-3-methylnaphthalen-2-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,4-dichlorophenylboronic acid (1.0 g), tetrakis(triphenylphosphine)palladium(0) (300 mg), 1-bromo-3-methyl-naphthalen-2-ol (5B, 625 mg) in K2CO3 (2 M, 5.3 mL) and DME (26 mL) was degassed with argon and sealed in a Schlenk tube. The reaction was heated to 80° C. for 75 minutes, then cooled to room temperature. The reaction was diluted with EtOAc and filtered through a pad of silica gel. The silica was washed with EtOAc and the combined organics were concentrated. The crude residue was purified by flash column chromatography (0-18% EtOAc in hexanes) to yield 784 mg of desired product.

Provenance & Evidence