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Imidazole → 4-((Tert-butyldimethylsilyl)oxy)-2-fluorobenzonitrile

HRID 1873941
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HRID 1873941 반응식
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].N1C=CN=C1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C=O)C>[Si:20]([O:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27346752-Fluoro-4-hydroxybenzonitrile

생성물 1

HCID 593707824-((Tert-butyldimethylsilyl)oxy)-2-fluorobenzonitrile수율 73%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

2-Fluoro-4-hydroxybenzonitrile (30.1 g; manufactured by Wako Pure Chemical Industries, Ltd.) and imidazole (18.3 g; manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in dehydrated DMF (436 mL; manufactured by Kanto Chemical Co., Inc.). After cooling to 0° C., TBDMSCl (48.3 g; manufactured by Tokyo Chemical Industry, Co., Ltd.) was added and the mixture was stirred for 1 hour while warming to room temperature. Solvent contained in the reaction solution was evaporated under reduced pressure. After adding water, extraction was carried out twice with ethyl acetate. The organic layer was washed twice with water and brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, purification was carried out with column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=100:0→94:6) to obtain the title compound (40.3 g).

후처리

  1. temperaturewhile warming to room temperature
  2. customwas evaporated under reduced pressure
  3. additionAfter adding
  4. extractionwater, extraction
  5. washThe organic layer was washed twice with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter the solvent was evaporated under reduced pressure, purification

출처 및 근거

ORD 기록
ord-e885c661ccc449c48c8ee1ca1fa19b62
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08304443B2

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