Benzyl Bromide → 4-Benzyloxybenzonitrile

HRID 453102Notes

Reaction equation

HRID 453102 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[CH2:16]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 5613714-BenzyloxybenzonitrileYield 131.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

To an ice cold solution of 4-hydroxybenzonitrile (0.50 g, 4.19 mmol) in 10 ml of acetone was added potassium carbonate (0.76 g, 5.49 mmol) followed by benzyl bromide (0.32 ml, 2.73 mmol). The reaction mixture was stirred at 25° C. overnight under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated to dryness under vacuum, added 50 ml water and extracted with ethyl acetate (3×40 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 10% EtOAc-Hexane) to get the desired product (0.75 g, 85%).

Workup

  1. customAfter the completion of the reaction (TLC monitoring)
  2. customthe reaction mixture was evaporated to dryness under vacuum
  3. additionadded 50 ml water
  4. extractionextracted with ethyl acetate (3×40 ml)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe crude residue was purified over silica gel (100-200 M, 10% EtOAc-Hexane)

Sources & evidence

ORD record
ord-35fef712d6434caab92f9b667594886b
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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