Water → 2-(Ethanesulfonyl)-5-nitrobenzonitrile

Participants

Reaction Conditions

Reaction Steps

Ethanethiol (2.8 mL, 38 mmol) was added to a solution of 2-fluoro-5-nitrobenzonitrile (5.00 g, 30.1 mmol) and triethylamine (9.3 mL, 67 mmol) in DMF (100 mL). The reaction mixture was stirred for 1 h and then poured into water (500 mL). The resulting precipitate was isolated by filtration, dissolved in DCM, washed with water and brine, dried (MgSO4), and concentrated under reduced pressure. The residue (6.14 g) was dissolved in DCM (100 mL), cooled to 0° C., and treated with MCPBA (16.0 g, 71 mmol) in one portion. The reaction mixture was allowed to stir at rt overnight, and then was extracted with sodium bicarbonate solution (saturated), sodium bisulfite solution (10%), and brine. The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford 6A (5.6 g, 80%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 1.02 (s, 6H), 1.97 (m, 2H), 2.36 (t, J=7.5 Hz, 2H), 2.68 (t, J=7.7 Hz, 2H), 3.76 (s, 4H), 7.18 (d, J=7.9 Hz, 2H), 7.72 (d, J=7.5 Hz, 2H).

Provenance & Evidence