Water → 2-(phenylsulfonyl)benzaldehyde

HRID 2387565Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Na+].[C:11]1([S:17]([O-:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CS(C)=O>[C:11]1([S:17]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-fluoro benzaldehyde (5.00 ml, 47.6 mmol) in dimethyl sulfoxide (45 ml) was added benzene sulfinic acid sodium salt (8.60 g, 52.4 mmol) and the resulting mixture heated to 100° C. Upon heating the sulfinic acid salt dissolved. The solution was heated at 100° C. for 3 days. The reaction was cooled to room temperature and water (50 ml) added. This mixture was extracted with ethyl acetate, the combined organic extracts were washed with saturated brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography on silica eluting with 25% ethyl acetate: petroleum ether (40-60° C.) to 33% ethyl acetate: petroleum ether (40-60° C.) to give (4.12 g, 16.7 mmol, 35%). δH (300 MHz, d6-DMSO) 10.68 (1H, s, CHO), 8.26-8.17 (1H, m, Ar), 8.08-7.99 (2H, m, Ar), 7.99-7.89 (3H, m, Ar) and 7.80-7.62 (3H, m, Ar).

Workup

dissolutiondissolved
temperatureThe solution was heated at 100° C. for 3 days
temperatureThe reaction was cooled to room temperature
extractionThis mixture was extracted with ethyl acetate
washthe combined organic extracts were washed with saturated brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography on silica eluting with 25% ethyl acetate
custompetroleum ether (40-60° C.) to 33% ethyl acetate: petroleum ether (40-60° C.) to give (4.12 g, 16.7 mmol, 35%)

Sources & evidence

ORD record: ord-96d9053fb9ec418097f91f348f664ac1
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268878B2

Reaction notes

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