Benzyl Alcohol → 2-(Benzyloxy)-4-fluorobenzonitrile

HRID 1271517Notes

Reaction equation

HRID 1271517 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[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]>C1COCC1>[CH2:1]([O:8][C:12]1[CH:19]=[C:18]([F:20])[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 775452,4-Difluorobenzonitrile

Product 1

HCID 210698282-(Benzyloxy)-4-fluorobenzonitrileYield 39.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2.5 mL benzyl alcohol in 80 mL THF is added 1.87 g NaH. After one hour stirring at room temperature, 5.0 g of 2,4-Difluorobenzonitrile is added. After stirring one hour, the reaction is quenched with excess water and concentrated in vacuo. The residue is redissolved in ethyl acetate and washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The product is recrystallizde in carbon tetrachloride to give 3.24 g (39.7%) of the title compound.

Workup

  1. stirringAfter stirring one hour
  2. customthe reaction is quenched with excess water
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is redissolved in ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85313e45bf884ff39abd94182019d2ff
Source dataset
uspto-grants-2007_04
Patent number
US07205313B2

Reaction notes

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