Dimethyl Sulfoxide → 3-(TRIFLUOROMETHYLTHIO)BENZALDEHYDE
Reaktionsgleichung
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]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
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).
Aufarbeitung
- 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)
Quellen und Nachweise
- ORD-Eintrag
- ord-d793445ddf6844ae8125032ab0ae1e25
- Quelldatensatz
- uspto-grants-2012_05
- Patentnummer
- US08168659B2
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