Benzyl Bromide → 3-(Benzyloxy)benzonitrile

HRID 322940Notes

Reaction equation

HRID 322940 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[CH2:12]([O:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 133943-CyanophenolHCID 24758Sodium hydride

Product 1

HCID 5613293-(Benzyloxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A stirred solution of 3-cyanophenol (20 g) in dry N,N-dimethylformamide (200 mL) is treated with sodium hydride (5.6 g; 60% dispersion in mineral oil), portionwise during 40 minutes, followed by dropwise addition of benzyl bromide (20 mL). The mixture is heated at 90° C. for 4 hours, cooled and concentrated under reduced pressure. The residue is partitioned between ethyl acetate and water and the organic layer washed with 1 N sodium hydroxide (100 mL) followed by drying over magnesium sulphate and concentration. The residue is recrystallised from methanol to give 3-benzyloxybenzonitrile (24 g), in the form of a cream solid, m.p. 38-40° C.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is partitioned between ethyl acetate and water
  4. washthe organic layer washed with 1 N sodium hydroxide (100 mL)
  5. dry with materialby drying over magnesium sulphate and concentration
  6. customThe residue is recrystallised from methanol

Sources & evidence

ORD record
ord-d16756b0f8654225b6763300fe83de4d
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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