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

Temperature

5 °C

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.

1. additionOn completion of the addition
2. customthe cooling bath was removed
3. concentrationThe mixture was concentrated
4. additionether was added
5. customThe resultant solid was removed by filtration
6. customthe filtrate was evaporated to dryness
7. customThe residue was purified by chromatography on silica
8. washeluting with a mixture of ether and pentane with a gradient of 0-50%

ORD record

ord-72a90548fd2a422390f2e0889431c555

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067905B2