Dimethyl Sulfoxide → 3-(TRIFLUOROMETHYLTHIO)BENZALDEHYDE

HRID 1919798Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]([S:15][C:16]1[CH:17]=[C:18]([CH2:22][OH:23])[CH:19]=[CH:20][CH:21]=1)([F:14])[F:13].C(N(CC)CC)C>ClCCl.O>[F:11][C:12]([S:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[CH:22]=[O:23])([F:14])[F:13]

Participants

Conditions

Temperature: -78 °C

Procedure

Add a solution of dimethyl sulfoxide (0.82 mL, 11.5 mmol) in dichloromethane (2 mL) over a period of 5 minutes to a solution of oxalyl chloride (0.46 mL, 5.28 mmol) in dichloromethane (10 mL) cooled to −78° C. Stir 10 minutes then add a solution of (3-trifluoromethylsulfanyl-phenyl)-methanol (1.00 g, 4.80 mmol) in dichloromethane (4 mL). Stir 15 minutes then add triethylamine (3.35 mL, 24.0 mmol). Slowly warm to ambient temperature, add water and separate the organic layer. Extract the aqueous layer with dichloromethane. Dry (sodium sulfate) the combined organic layers, filter, and concentrate in vacuo. Purify by silica gel chromatography (10% ethyl acetate/hexane) to afford the titled compound as a yellow liquid (896 mg, 91%). 1H NMR (400 MHz, DMSO) δ 7.74 (dd, J=7.6, 7.6, 1H), 8.01 (d, J=7.9, 1H), 8.09 (d, J=7.5, 1H), 8.12 (s, 1H), 10.03 (s, 1H).

Workup

stirringStir 15 minutes
temperatureSlowly warm to ambient temperature
customseparate the organic layer
extractionExtract the aqueous layer with dichloromethane
dry with materialDry (sodium sulfate) the combined organic layers
filtrationfilter
concentrationconcentrate in vacuo
customPurify by silica gel chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-d793445ddf6844ae8125032ab0ae1e25
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168659B2

Reaction notes

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