Benzyl Alcohol → 3-Fluoro-2-(phenylmethoxy)benzonitrile

HRID 337120노트

반응식

HRID 337120 반응식
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].F[C:12]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15]>C1COCC1>[CH2:1]([O:8][C:12]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:13]=1[C:14]#[N:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 889352,3-Difluorobenzonitrile

생성물 1

HCID 577052113-Fluoro-2-(phenylmethoxy)benzonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

Benzyl alcohol (5.51 mL) was added dropwise over 20 min to a stirred suspension of sodium hydride (2.128 g of a 60% dispersion in mineral oil) and 2,3-difluorobenzonitrile (7.4 g) in THF (100 mL) with external ice bath cooling to maintain temperature around 25° C. After addition was complete, the reaction mixture was stirred at room temperature for 24 h, quenched with water (200 mL) and extracted into ethyl acetate (3×120 mL), combined organics were dried (MgSO4) and evaporated. The residual oil was purified (SiO2 chromatography eluting with 20% ether in isohexane) to give the subtitle compound as an oil (9.70 g).

후처리

  1. temperaturecooling
  2. additionAfter addition
  3. customquenched with water (200 mL)
  4. extractionextracted into ethyl acetate (3×120 mL)
  5. dry with materialcombined organics were dried (MgSO4)
  6. customevaporated
  7. customThe residual oil was purified
  8. wash(SiO2 chromatography eluting with 20% ether in isohexane)

출처 및 근거

ORD 기록
ord-f120ff53d87e4cdfb8c54600fef750b8
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889692B2

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