Benzyl Alcohol → 4-Benzyloxy-3,5-difluorobenzonitrile

HRID 602019Notes

Reaction equation

HRID 602019 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1F)[C:5]#[N:6].[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].Cl>CN(C=O)C>[CH2:12]([O:19][C:9]1[C:8]([F:11])=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[F:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 5938143,4,5-Trifluorobenzonitrile

Product 1

HCID 574457224-Benzyloxy-3,5-difluorobenzonitrileYield 89.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.0 g of 3,4,5-trifluorobenzonitrile and 4.5 g of benzyl alcohol in 25 ml of DMF was added 1.5 g of 60% sodium hydride (oily) at 0° C. The mixture was stirred at room temperature for 4 hours. Then, dilute hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 7.0 g of 4-benzyloxy-3,5-difluorobenzonitrile represented by the formula:

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dfeb9a83587847b38aa638aff9ebc8c5
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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