Sodium Bicarbonate → Ethyl 6-(4-chlorobenzenesulphonylmethyl)-3-bromo-2-methoxybenzoate

HRID 2177751Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:16][CH3:17])=[C:4]([C:10]([CH:13](Br)Br)=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(=O)(O)[O-].[Na+].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O-:32])=[O:31])=[CH:26][CH:25]=1.[Na+]>CC(N(C)C)=O.O>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH2:13][C:10]2[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:3]([O:16][CH3:17])[C:2]([Br:1])=[CH:12][CH:11]=2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 3-bromo-6-(dibromomethyl)-2-methoxybenzoate (Intermediate 88, 0.25 g), sodium bicarbonate (0.122 g) and sodium 4-chlorobenzenesulphinate (0.29 g) in dimethylacetamide (4 ml) and water (1 ml) was stirred and heated at 90° C. for 5 hours. After cooling, the mixture was diluted with water and loaded onto a water washed C-18 column which was then flushed with water and eluted with DCM and ethyl acetate. The organic eluent was dried (MgSO4) 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 0-100% to give ethyl 6-(4-chlorobenzenesulphonylmethyl)-3-bromo-2-methoxy-benzoate (0.15 g) as a gum.

Workup

temperatureAfter cooling
customwas then flushed with water
washeluted with DCM and ethyl acetate
dry with materialThe organic eluent was dried (MgSO4)
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 0-100%

Sources & evidence

ORD record: ord-61bd7d8e4d4847a8bb78613cbf6fdf5c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067905B2

Reaction notes

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