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Dimethylformamide → 5-Trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 589279
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인쇄 미리보기

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HRID 589279 반응식
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=O.[C:14]([O:18][CH3:19])(=[O:17])[CH2:15][SH:16].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:11][C:10]([F:13])([F:12])[C:7]1[CH:8]=[CH:9][C:2]2[S:16][C:15]([C:14]([O:18][CH3:19])=[O:17])=[CH:4][C:3]=2[CH:6]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehyde

생성물 1

HCID 14779565-Trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester수율 93%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
60 °C

실험 절차

A mixture of 5.0 g of 2-fluoro-5-(trifluoromethyl)benzaldehyde, 3.3 g of methyl thioglycolate, 4.0 g of potassium carbonate and 50 ml of DMF was stirred at 60° C. for 2 hours, and then the reaction mixture was cooled to room temperature. To the reaction mixture was added water, and extracted with tert-butyl methyl ether 3 times. The combined organic layer was washed with water, followed by saturated aqueous sodium chloride solution. The mixture was dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from methanol to obtain 6.3 g of methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate.

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with tert-butyl methyl ether 3 times
  3. washThe combined organic layer was washed with water
  4. dry with materialThe mixture was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from methanol

출처 및 근거

ORD 기록
ord-97ed15902577462c99ed5940edf75a7f
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09232792B2

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