N,N'-Dimethylethylenediamine → benzene, 1-fluoro-3-(phenylsulfonyl)-

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-fluoro-3-iodobenzene (2.22 g, 10 mmol), sodium phenylsulfinate (2.16 g, 13 mmol), copper (1) trifluoromethylsulfonate-benzene complex (0.15 g, 0.3 mmol), N,N′-dimethylethylenediamine (0.95 g, 1.09 mmol) and dimethyl sulfoxide (20 mL) was heated at 90° C. under nitrogen with stirring for 2 h then at 115° C. for 18 h. Mixture was cooled then partitioned between water (150 mL) and 1:1 Et2O− EtOAc (100 mL) and the organic phase was washed with water (3×100 mL), dried (Na2SO4) and evaporated in vacuo to give a beige solid. Chromatography (SiO2; gradient elution with 0-40% Et2O in petrol) gave the title compound (1.725 g, 73%) as a colourless solid. 1H NMR (CDCl3): 8.02-7.93 (2H, m), 7.81-7.71 (1H, m), 7.71-7.46 (5H, m), 7.28 (1H, m).

Provenance & Evidence