Potassium Carbonate → (4-(2,6-Difluorobenzyloxy)phenyl)-acetonitrile

HRID 1824834Notes

Reaction equation

HRID 1824834 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:19]=1[CH2:20]Br>CN(C=O)C>[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:19]=1[CH2:20][O:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanideHCID 5814352-(Bromomethyl)-1,3-difluorobenzene

Product 1

HCID 21964471(4-(2,6-Difluorobenzyloxy)phenyl)-acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-Hydroxybenzyl cyanide (5 g, 37.5 mmol) and K2CO3 (6.74 g, 48.8 mmol) in dry DMF (20 ml) was added 2,6-Difluorobenzyl bromide (7.77 g, 37.5 mmol). The reaction mixture was stirred for 4 hours at room temperature and concentrated in vacuo. The crude residue was taken in EtOAc and washed with water and brine. The aqueous layer was washed one more time with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated to provide the title compound as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with water and brine
  3. washThe aqueous layer was washed one more time with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a32cee17ae1d4bcbbeba7db1d67a2c75
Source dataset
uspto-grants-2006_05
Patent number
US07045541B2

Reaction notes

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