4-Hydroxybenzyl cyanide → (4-(2,6-Difluorobenzyloxy)phenyl)-acetonitrile

HRID 1958853Notes

Reaction equation

HRID 1958853 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[F:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:13]=1[CH2:14]Br>CN(C=O)C>[F:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:13]=1[CH2:14][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 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 K7CO3 (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-205e928a24254b91be54a1a2e7967d10
Source dataset
uspto-grants-2013_04
Patent number
US08410154B2

Reaction notes

Loading…