5-Fluoro-2-nitrotoluene → 1-(3,5-Dimethoxyphenylsulphanyl)-3-methyl-4-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

0.426 g (0.0021 mol) of 3,5-dimethoxythiophenol potassium salt was dissolved in 7 ml of 1-methyl-2-pyrrolidone, treated with 0.317 g (0.0021 mol) of 5-fluoro-2-nitrotoluene and a spatula tip of Cu powder and stirred at 160° C. for about 5 hrs. Thereafter, the reaction mixture was partitioned in water/diethyl ether and the organic phase was washed with sat. sodium chloride solution and dried over MgSO4. After filtration and removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:9. There was obtained 0.343 g (55%) of 1-(3,5-dimethoxyphenylsulphanyl)-3-methyl-4-nitrobenzene as a yellow oil. MS (EI): me/e=305 (C15H15NO4S+).

Provenance & Evidence