4-Methoxybenzoic Acid → 3-Chloro-p-anisic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methoxybenzoic acid (0.46 g; 3 mmol) and N-chlorosuccinimide (NCS) (0.36 g; 2.7 mmol) in trifluoroacetic acid (5 ml) was stirred for 3 h at ˜70° C. After removing solvent under reduced pressure the residue was treated with H2O (10 ml). The solid was filtered off and purified by FCC (SiO2; EtOAc) to give the title compound (0.38 g; 68%) as a colourless solid. 1H-NMR (CDCl3) 3.97 (s, 3H); 6.96 (d, 1H, J=8.7 Hz); 8.0 (dd, 1H, J=2; 8.7 Hz); 8.11 (d, 1H, J=2 Hz).

Provenance & Evidence