(Diethylamino)sulfur trifluoride → HCID 68701047, compound

Participants

Reaction Steps

To a cooled solution (T=−60° C.) of 2-hydroxy-2-(3-nitrophenyl)propanenitrile (1.11 g, 5.8 mmol) in dry CH2Cl2 (60 ml), (diethylamino)sulfur trifluoride (0.8 mL, 6.0 mmol) was added under vigorous stirring. The resulting reaction mixture was left stirring at room temperature overnight. The reaction mixture was diluted with a buffer solution (pH=5.0) (10 ml), trasferred into a separator funnel and the two phases were debated and separated. The aqueous one was extracted with water (3×10 mL); the collected organic extracts were dried over Na2SO4 and evaporated under vacuum to give a crude which was purified by flash chromatography to afford pure 2-fluoro-2-(3-nitrophenyl)propanenitrile (0.9 g, yield 79%) as brown oil. 1H-NMR (CDCl3) δ 8.52 (s, 1H), 8.45 (d, 1H, J=3 Hz), 7.90 (m, 1H), 7.70 (t, 1H, J=7 Hz), 2.12 (d, 3H, J=23 Hz).

Provenance & Evidence