Sodium Carbonate → 4-(Chloromethyl)-2-nitroanisole

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methoxy-3-nitrobenzyl alcohol (4.9 g, 24.4 mmol) in 150 mL of dichloromethane was added triphenylphosphine (4.2 g, 31.7 mmol). The reaction was cooled to 0° C. and N-chlorosuccinimide (8.3 g, 31.7 mmol) was added. The reaction was warmed to room temperature and then heated gently to 50° C. for 2 h. The reaction was poured into aqueous sodium carbonate solution and the aqueous layer was extracted with dichloromethane and then ethyl acetate. Combined organics were dried over anhydrous MgSO4, filtered, concentrated onto silica gel and purified by flash chromatography with ethyl acetate/hexanes as the eluent to give 4-methoxy-3-nitrobenzyl chloride (3.09 g, 63%). 1H NMR (400 MHz, CDCl3) δ ppm 7.98 (d, J=2.4 Hz, 1H), 7.73 (d, J=8.8, 2.4 Hz, 1H), 7.37 (d, J=8.8 Hz, 1H), 4.78 (s, 2H), 3.91 (s, 3H).

Provenance & Evidence