p-Toluenesulfonic acid → 2-Nitro-4-(1-pyrrolyl)fluorobenzene

Participants

Reaction Steps

To a suspension of 4-fluoro-3-nitroaniline (20g, 0.13mol) in toluene (200mi) is added 2,5-dimethoxytetrahydrofuran (33ml, 0.26mol) and a catalytic amount of pTSA. The mixture is refluxed for 2.5 hours. After cooling the solvent is removed by evaporation and the residue is purified by column chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (1:1) as the eluent. Yield: 23.1g (87%). Mp 79-81° C.

Provenance & Evidence