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

HRID 337260Notes

Reaction equation

HRID 337260 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[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:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[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 2-(4-Hydroxyphenyl)acetonitrile (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 layer was 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 layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bdb78c906c22436185d22e13387d3584
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

Loading…