Cesium carbonate → HCID 118452708, compound

Participants

Reaction Steps

To a solution of 2-hydroxy-4-methylbenzaldehyde (12 g, 88 mmol) in 432 mL of CH3CN was added Cs2CO3 (34.5 g, 106 mmol) followed by 2-bromoacetonitrile (6.75 mL, 97 mmol), After the mixture was stirred at room temperature for 6 hr, the mixture was filtered through Celite to remove solid, washed with DCM, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel flash chromatography, 100% Heptane-20% Ethyl Acetate/80% Heptane) to give a white solid, 2-(2-formyl-5-methylphenoxy)acetonitrile (14.2 g). LCMS retention time=1.06 minutes (LC method 3); MS (m+1)=175.8. 1H NMR (400 MHz, DMSO-d6) δ 2.41 (s, 3H), 5.33 (s, 2H), 7.05 (d, J=7.8 Hz, 1H), 7.20 (s, 1H), 7.68 (s, 1H), 10.26 (d, J=0.8 Hz, 1H).

Provenance & Evidence