Dimethyl Sulfoxide → 5-(4-Fluorophenoxy)thiophene-2-carbonitrile

HRID 640342

반응식

HRID 640342 반응식
CS(C)=O.[N+]([C:8]1[S:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=1)([O-])=O.[F:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:8]2[S:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=2)=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 5192945-Nitrothiophene-2-carbonitrile

생성물 1

HCID 231305625-(4-Fluorophenoxy)thiophene-2-carbonitrile수율 85.9%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

To a dimethyl sulfoxide (100 mL) solution of 5-nitro-2-thiophene carbonitrile (5.00 g, 32.4 mmol) were added 4-fluorophenol (5.45 g, 48.6 mmol) and potassium carbonate (11.2 g, 81.0 mmol) under nitrogen atmosphere, which was stirred for 16 hours at 60° C. The reaction solution was cooled to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:10→1:5) to obtain the title compound (6.10 g, 85.9%).

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:10→1:5)

출처 및 근거

ORD 기록
ord-6a99905788ad4140bd2ffd2f0a2ea9e8
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691882B2

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