Potassium Carbonate → HCID 66696660, compound

Participants

Reaction Steps

A mixture of 3-fluoro-4-methylbenzaldehyde (1.38 g, 10.0 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (2.09 g, 10.0 mmol), and K2CO3 (1.66 g, 12.0 mmol) in 50 mL methanol was heated at reflux 3 hr, then cooled to room temperature and stirred overnight. The reaction mixture was concentrated and the residue taken up in 25 mL H2O and 25 mL Et2O. The water layer was extracted with Et2O, and the organic layers were combined, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (Analogix® SF40-115 g column) with 15% EtOAc/hexanes to yield 1.56 g (82%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.34 (s, 1H), 7.45-7.30 (m, 3H), 2.36 (s, 3H), 2.27 (d, J=1.9, 3H).

Provenance & Evidence