Water → HCID 66696685, compound

Participants

Reaction Steps

A mixture of 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (1.56 g, 7.44 mmol), 4-chloro-3-fluorobenzaldehyde (1.18 g, 7.44 mmol), and K2CO3 (2.06 g, 14.9 mmol) in MeOH (35 mL) was heated to reflux. After 1.5 hr water (200 mL) was added and the product was extracted with EtOAc (200 mL). The organic layer was washed with brine and dried over Na2SO4, filtered, and concentrated to an orange oil. Chromatography on silica gel (Analogix® SF25-40G, 0%-30% EtOAc/hexanes, 30 mL/min) afforded 1.35 g (86%) of the title compound as a yellow solid. 1H NMR (300 MHz, CH3OH-d4) δ 8.18 (s, 1H), 7.62-7.55 (m, 1H), 7.52 (dd, J=1.9, 10.3, 1H), 7.49-7.44 (m, 1H), 2.42 (s, 3H). MS (DCI+) m/z 212 (M+H).

Provenance & Evidence