Benzyl Alcohol → 2-(Benzyloxy)-3-fluorobenzonitrile

HRID 1697379Notes

Reaction equation

HRID 1697379 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 577052112-(Benzyloxy)-3-fluorobenzonitrile

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-0a5daf4e66784ccfa1ef61c3d419fc25
Source dataset
uspto-grants-2012_04
Patent number
US08163905B2

Reaction notes

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