Benzyl Bromide → 4-Benzyloxybenzonitrile

HRID 2041149Notes

Reaction equation

HRID 2041149 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].C(#N)C>[CH2:10]([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 5613714-BenzyloxybenzonitrileYield 100.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

Add 4-cyanophenol (1.191 g, 10 mmol), benzyl bromide (1.881 g, 11 mmol), potassium carbonate (3.455 g, 25 mmol) and potassium iodide (166 mg, 1 mmol) to acetonitrile (80 mL) and heat at reflux for 12 h. Cool, partition between EtOAc and water, separate the organic layer, and extract the aqueous layer with EtOAc. Combine the organic extracts, wash with brine, dry over Na2SO4, filter and concentrate. Purify by chromatography on silica gel eluting with EtOAc/hexane (1:6) to give the desired intermediate as a white solid (2.098 g, 100%). MS (ES+) m/z: 227 (M+NH4)+.

Workup

  1. temperatureheat
  2. temperatureat reflux for 12 h
  3. temperatureCool
  4. custompartition between EtOAc and water
  5. customseparate the organic layer
  6. extractionextract the aqueous layer with EtOAc
  7. washwash with brine
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate
  11. customPurify by chromatography on silica gel eluting with EtOAc/hexane (1:6)

Sources & evidence

ORD record
ord-af6228d5bbb047c3add28ca07571427e
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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