2-Bromo-1-fluoro-4-nitrobenzene → 2-Bromo-1-methylsulfanyl-4-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

A solution of 25.7 g (120 mmol) 2-bromo-1-fluoro-4-nitrobenzene in 154 ml DMF is treated with 10.6 g (150 mmol) sodium thiomethylate and stirred for 5 hours at 60° C. The mixture is stirred at room temperature for 18 hours, again treated with 1.0 g sodium thiomethylate and stirred for a further 6 hours at 60° C. After cooling, the mixture is poured into ice-water and extracted with ethyl acetate (3×). The combined organic phases are washed with water, dried (Na2SO4), filtered and concentrated. The residue obtained is chromatographically purified (hexane/ethyl acetate 2:1). 20.4 g (82 mmol, corresponding to 70% of theor.) of the product is obtained.

Provenance & Evidence