Bromine → HCID 19756153, compound

Participants

Reaction Steps

Bromine (192 μl) was added to a suspension of 3,4-dihydroxy-6-(methoxycarbonylmethyl)benzaldehyde (0.79 g) in acetic acid (15 ml). The reaction mixture was stirred at ambient temperature for 5-6 hours, diluted with water (30 ml) and extracted into ethyl acetate (200 ml). The organic phase was washed with NaHCO3, water (100 ml) and brine, dried and evaporated under reduced pressure to give a brown solid. This was purified by chromatography using aqueous acetonitrile mixtures to give 3-bromo-4,5-dihydroxy-2-(methoxycarbonylmethyl)benzaldehyde (300 mg); NMR (DMSO-d6) 3.61(s,3H); 4.24(s,2H); 7.24(s,1H); 9.8(s,1H): CI M/S (M+H)+ 291.

Provenance & Evidence