Dimethylformamide → 5-(4-Cyanobenzyloxy)-2-nitrobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 10.0 g (59.8 mmol) of 5-hydroxy-2-nitrobenzaldehyde and 12.3 g (62.8 mmol) of a-bromo-p-tolylnitrile in 50 ml of dry dimethyl-formamide was added 9.10 g (65.8 g) of anhydrous potassium carbonate. The mixture was warmed to 50° C. for 2 h and partitioned between water and ethyl acetate. The organic phase was washed with 1N sodium bicarbonate, water, brine, and dried over anhydrous magnesium sulfate. Concentration gave 13.8 g (82%) of 5-(4-cyanobenzyloxy)-2-nitrobenzaldehyde. 1H NMR (300 MHz, d6 -acetone) d 10.39 (1H, s, Ar--CHO), 8.23 (1H, d, J=9.0 Hz, O--Ar--H), 7.85 (2H, d, J=8.3 Hz, NC--Ar--H2), 7.77 (2H, d, J=8.3 Hz, NC--Ar--H2), 7.48 (1H, dd, J=9.0, 2.9 Hz, O--Ar--H), 7.43 (1H, d, J=2.9 Hz, O--Ar--H), 5.50 (2H, s, ArCH2O).

Provenance & Evidence