Water → Methyl 2-(2,2,2-trifluoroethylthio)benzoate

Participants

Reaction Conditions

Reaction Steps

Methylthiosalicylate (5.0 mL, 36 mmol) was added dropwise to a stirred suspension of NaH (60% oil dispersion, 1.43 g, 36 mmol) in dry DMF (30 ml,) at room temperature. The mixture was stirred in the dark under Ar for 30 min and was then cooled to 0° C. and treated with a solution of 1,1,1-trifluoro-2-iodoethane (3.0 mL, 30 mmol) in DMF (10 mL) via cannula. The reaction flask was covered with foil and was allowed to warm to room temperature while stirring overnight. Water was poured into the mixture which was then extracted with ether (3×150 mL). The combined ether extracts were washed with saturated aqueous Na2CO3 and brine, dried over MgSO4 filtered and concentrated in vacuo. Silica gel chromatography (isocratic elution with 10% EtOAc-hexanes) afforded the title compound as a pale yellow oil:

Provenance & Evidence