Sodium Bicarbonate → Methyl 6-(benzenesulfonylmethyl)-3-bromo-2-methoxybenzoate

HRID 1778366Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:15][CH3:16])=[C:4]([C:9]([CH:12](Br)Br)=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:17]1([S:23]([O-:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na+].C(=O)([O-])O.[Na+]>CC(N(C)C)=O.O>[C:17]1([S:23]([CH2:12][C:9]2[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([O:15][CH3:16])[C:2]([Br:1])=[CH:11][CH:10]=2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of methyl 3-bromo-6-dibromomethyl-2-methoxybenzoate (Intermediate 42A, 19 g) in DMA (300 mL) was added to a stirred solution of sodium benzenesulfinate 17.9 g) and sodium hydrogen carbonate (9.5 g) in water (70 mL) and the mixture was heated at 90° C. for 2 hours. After cooling, the mixture was poured into water and filtered through Celite and the pad was washed with ethyl acetate. The organic layer was separated, washed with water and brine, 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 pentane with a gradient of 0-100% to give methyl 6-(benzenesulfonylmethyl)-3-bromo-2-methoxybenzoate (13.8 g).

Workup

temperatureAfter cooling
filtrationfiltered through Celite
washthe pad was washed with ethyl acetate
customThe organic layer was separated
washwashed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
customThe filtrate was evaporated to dryness
customthe residue was purified by chromatography on silica
washeluting with a mixture of ethyl acetate and pentane with a gradient of 0-100%

Sources & evidence

ORD record: ord-dc492581d0654cd385ac4e3505a535ef
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266896B2

Reaction notes

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