Potassium Carbonate → Methyl 6-(bicyclo[2.2.1]hept-7-ylthiomethyl)-3-bromo-2-methoxybenzoate

HRID 2177830Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 3-bromo-6-bromomethyl-2-methoxybenzoate (Intermediate 89, 0.338 g), bicyclo[2.2.1]heptane-7-thiol (Intermediate 183, 0.148 g) and potassium carbonate (0.345 g) in THF (5 ml) was stirred and heated at 60° C. for 3 days. After cooling, the mixture was partitioned between ethyl acetate and water and the organic layer was separated, 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 0-10% to give methyl 6-(bicyclo[2.2.1]hept-7-ylthiomethyl)-3-bromo-2-methoxybenzoate (0.244 g).

Workup

temperatureAfter cooling
customthe mixture was partitioned between ethyl acetate and water
customthe organic layer was separated
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 0-10%

Sources & evidence

ORD record: ord-29ed07d17e8a4693ab6ed6c1652e412a
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067905B2

Reaction notes

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