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1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-one → 2-(3,5-Dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide

HRID 62626
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HRID 62626 반응식
[C:1]1([S:7]([CH2:9]P(=O)(OCC)OCC)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[Cl:24][C:25]1[CH:26]=[C:27]([C:32](=O)[C:33]([F:36])([F:35])[F:34])[CH:28]=[C:29]([Cl:31])[CH:30]=1>C1(C)C=CC=CC=1>[C:1]1([S:7]([CH:9]=[C:32]([C:27]2[CH:28]=[C:29]([Cl:31])[CH:30]=[C:25]([Cl:24])[CH:26]=2)[C:33]([F:36])([F:35])[F:34])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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참가 물질

5

반응물 3

HCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 10858739Diethoxyphosphoryl-methylsulfinyl-benzeneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 1317371992-(3,5-Dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide수율 93%

시약·촉매·용매 1

HCID 1140Toluene용매2회

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온도
0 °C

실험 절차

Diethyl [(phenylsulfinyl)methyl]phosphonate (5.00 g, 96% purity, 17.4 mmol) was dissolved in toluene (20 mL) and cooled to 0° C. To the solution potassium tert-butoxide (2.05 g, 18.2 mmol) was added in one portion. This solution was added over 45 minutes to a solution of 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanone (4.26 g, 99% purity, 17.4 mmol) in toluene at 0° C. The reaction mixture was stirred for additional 15 minutes at 0° C. and then warmed to room temperature over 30 minutes. The solution was poured onto hydrochloric acid (3.6%) and the phases were separated. The aqueous phase was extracted with toluene and the combined organic phases were washed with water, dried over sodium sulfate and the solvents evaporated. 2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide was obtained (6.26 g, 94% purity, 93% yield, E/Z=38/62).

후처리

  1. temperaturewarmed to room temperature over 30 minutes
  2. additionThe solution was poured onto hydrochloric acid (3.6%)
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with toluene
  5. washthe combined organic phases were washed with water
  6. dry with materialdried over sodium sulfate
  7. customthe solvents evaporated

출처 및 근거

ORD 기록
ord-0f1a36e800da48959488e7943f92e231
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09447036B2

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