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

HRID 337120ノート

反応式

HRID 337120 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 577052113-Fluoro-2-(phenylmethoxy)benzonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f120ff53d87e4cdfb8c54600fef750b8
出典データセット
uspto-grants-2014_11
特許番号
US08889692B2

反応ノート

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