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

HRID 1675575Notes

Reaction equation

HRID 1675575 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 mixture obtained by adding 5.0 g of 3,4,5-trifluorobenzonitrile and 4.5 g of benzyl alcohol to 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. Thereafter, dilute hydrochloric acid was added to the reaction mixture, followed by extraction 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, and 7.0 g of 4-benzyloxy-3,5-difluorobenzonitrile was obtained.

Workup

  1. customTo a mixture obtained
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-722b879621eb4125bd6fe375fe577779
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

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