Diisopropylamine → Ethyl 3-bromo-2-hydroxy-6-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

A solution of N-bromosuccinimide (3.97 g) in DCM (170 ml) was added dropwise to a stirred, cooled solution of ethyl 2-hydroxy-6-methylbenzoic acid (prepared according to Hauser et al, Synthesis, 1980 814, 4.02 g) and di-isopropylamine (0.31 ml) in DCM (50 ml) while maintaining the temperature at 0° C. (±5° C.). On completion of the addition, the cooling bath was removed and the mixture was stirred at room temperature overnight. The mixture was concentrated and ether was added. The resultant solid was removed by filtration and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ether and pentane with a gradient of 0-50% to give ethyl 3-bromo-2-hydroxy-6-methylbenzoate (5.19 g) as a colourless oil.

Provenance & Evidence