1-Fluoro-3-nitrobenzene → 2-Chloro-1-fluoro-3-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of 3-fluoronitrobenzene (2 g, 14.2 mmol) in THF (30 mL) was added N-chlorosuccinimide (5.69 g, 42.6 mmol) in THF (20 mL), NaHMDS (1 M in THF, 28.4 mL, 28.4 mmol) was then added dropwise to maintain an internal temperature below −75° C. The resulting mixture was stirred for 30 min at −78° C. Then it was partitioned between 5% of HCl and ethyl acetate. The combined organic layer is dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (20% Ethyl acetate Hexane) gave the desired product(231 mg, 9.2%). EI-MS m/z 176.5 (M+).

Provenance & Evidence