Ethyl Acetate → 4-[(3-Fluorophenyl)methoxy]benzonitrile

HRID 2080041Notes

Reaction equation

HRID 2080041 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 680073-Fluorobenzyl bromide

Product 1

HCID 22293834-[(3-Fluorophenyl)methoxy]benzonitrileYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-cyanophenol (3.0 g, 25.2 mmol) and 3-fluorobenzyl bromide (3.1 mL, 25.2 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (8.71 g, 63.0 mmol), and the mixture was stirred for 1 hour at room temperature. Ethyl acetate and water were added to the reaction mixture, which was then partitioned, the organic layer was washed with water, then, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain 4-(3-fluorobenzyloxy)-benzonitrile (5.31 g, 93%) as a colorless solid.

Workup

  1. customwas then partitioned
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0d600fd97bbc4fc88252f6f158980646
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…