3,4-Difluoroanisole → 1-Fluoro-4-methoxy-2-methylsulfanylbenzene

Participants

Reaction Conditions

Reaction Steps

1,2-Difluoro-4-methoxy-benzene (100 mg, 0.69 mmol) and sodium methanethiolate (148 mg, 2.08 mmol) were dissolved in N,N-dimethylformamide (2 mL) and the reaction mixture stirred at 60° C. for 18 hours. Additional sodium methanethiolate (99 mg, 139 mmol) was added and the reaction mixture heated to 100° C. for 18 hours. The reaction mixture was diluted with water and extracted with ether (x2). The ether extracts were washed with water (x2), dried over magnesium sulphate and concentrated in vacuo. The residue was taken up in pentane:ether 1:1 mixture (2 mL) and filtered through a plug of silica in a pipette, washing through with pentane:ether 1:1 mixture (5 mL). The solution was concentrated in vacuo to yield the title product as a colourless oil, 135 mg.

Provenance & Evidence