Thiophenol → 4-Bromo-N-methyl-2-nitro-3-(phenylthio)aniline

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromo-3-fluoro-N-methyl-2-nitroaniline (0.30 g, 1.20 mmol) in N,N-dimethylformamide (2.45 mL) was treated with cesium carbonate (0.472 g, 1.45 mmol) and benzenethiol (0.149 mL, 1.45 mmol). The resultant reaction mixture was warmed to 80° C. and stirred at 80° C. for 30 min, after which time the reaction mixture was diluted with ethyl acetate and water. Layers were separated and the organic layer was washed with 10% solution of K2CO3 and brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (100% hexanes to 40% EtOAc/hexanes) gave the desired product (396 mg, 97%) as an orange solid. LCMS calculated for C13H12BrN2O2S (M+H)+: m/z=339.0, 341.0. found: 338.9, 340.9.

Provenance & Evidence