Dimethylformamide → (4-(2,6-Difluorobenzyloxy)phenyl)-acetonitrile

HRID 1911616Notes

Reaction equation

HRID 1911616 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:9]=1[CH2:10]Br.C[N:18]([CH:20]=O)C>>[F:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:9]=1[CH2:10][O:4][C:1]1[CH:13]=[CH:12][C:9]([CH2:10][C:20]#[N:18])=[CH:8][CH:15]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5814352-(Bromomethyl)-1,3-difluorobenzene

Product 1

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

Procedure

To a solution of 4-Hydroxybenzyl cyamide (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 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 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-9f2a502ba1b94ceba4192fe59b48389c
Source dataset
uspto-grants-2013_12
Patent number
US08604083B2

Reaction notes

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