Dimethyl Sulfoxide → 3-(TRIFLUOROMETHYLTHIO)BENZALDEHYDE

HRID 1919798노트

반응식

HRID 1919798 반응식
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]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27778683-(Trifluoromethylthio)benzyl alcohol

생성물 1

HCID 27778433-(TRIFLUOROMETHYLTHIO)BENZALDEHYDE수율 91%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

반응 조건

온도
-78 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d793445ddf6844ae8125032ab0ae1e25
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168659B2

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