Triisopropyl borate → (6-Methyl-1-benzothiophen-2-yl)boronic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-methyl-benzo[b]thiophene (0.16 g, 0.001 mol) in 10 mL of anhydrous THF at −60° C. is added n-BuLi (0.8 mL, 0.0012 mol) dropwise via syringe. After stirring for 30 minutes triisopropyl borate (0.3 mL, 0.0012 mol) is added dropwise. The reaction mixture is allowed to warm to 0° C. and then partitioned between 1.0N HCl and EtOAc. The organic layer is separated, dried, filtered and concentrated to produce a white solid that is triturated from ether/hexane. Filtration provides 0.17 g of 6-Methyl-benzo[b]thiophene-2-boronic acid as white solid. MS m/z 193 [M+1]+.

Provenance & Evidence