Potassium Carbonate → Methyl 3-bromo-2-hydroxy-6-(2-methoxyphenylthiomethyl)benzoate

HRID 2177749Notes

Reaction equation

[Br:1][C:2]1[C:3]([OH:14])=[C:4]([C:9]([CH2:12]Br)=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[SH:23].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:1][C:2]1[C:3]([OH:14])=[C:4]([C:9]([CH2:12][S:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH3:15])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 3-bromo-6-bromomethyl-2-hydroxybenzoate (Intermediate 53, 0.6 g), 2-methoxythiophenol (0.518 g) and potassium carbonate (0.766 g) in THF (10 ml) was stirred and heated at 60° C. for 3 hours. After cooling, the mixture was partitioned between ethyl acetate and water and the separated organic layer was washed with potassium hydroxide solution, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-15% to give methyl 3-bromo-2-hydroxy-6-(2-methoxyphenylthiomethyl)-benzoate (0.46 g) as a white solid which was used without further characterisation.

Workup

temperatureAfter cooling
customthe mixture was partitioned between ethyl acetate and water
washthe separated organic layer was washed with potassium hydroxide solution
dry with materialdried (Na2SO4)
filtrationfiltered
customThe filtrate was evaporated to dryness
customthe residue was purified by chromatography on silica
washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-15%

Sources & evidence

ORD record: ord-ea88bd49a3124918876501837993a031
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067905B2

Reaction notes

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