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

HRID 337120Notes

Reaction equation

HRID 337120 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 577052113-Fluoro-2-(phenylmethoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-f120ff53d87e4cdfb8c54600fef750b8
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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