N-Fluorobenzenesulfonimide → 4-Bromo-2-fluoromethyl-quinolin-8-ol

Participants

Reaction Conditions

Reaction Steps

A solution of lithium diisopropylamide (1.8 M in THF, 0.70 mL, 1.3 mmol) in anhydrous THF (1.0 mL) was added dropwise to a stirred solution of 4-bromo-2-methyl-quinolin-8-ol (100 mg, 0.420 mmol) in anhydrous THF (1.0 mL) at −80° C. After stirring for 1 h at −80° C., a solution of N-fluorobenzenesulfonimide (331 mg, 1.05 mmol) in anhydrous THF (1 mL) was added dropwise at −100° C. The reaction mixture was allowed to warm to −20° C. and was then quenched by the addition of concentrated aqueous NH4Cl (0.4 mL). The mixture was partitioned between DCM (30 mL) and water (5 mL). The aqueous layer was extracted with DCM (2×10 mL) and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with DCM) to give the title compound. MS (m/z): 258.1 [M+H+].

Provenance & Evidence