Benzyl Bromide → HCID 18318128, compound

HRID 1700293Notes

Reaction equation

HRID 1700293 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[C:7]#[N:8])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:7]#[N:8])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 767584-Hydroxy-3-nitrobenzonitrile

Product 1

HCID 18318128HCID 18318128, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-nitro-4-hydroxybenzonitrile (10 g, 61 mmol) in a mixture of 40 mL of dimethylformamide and 100 mL of acetonitrile was stirred as anhydrous potassium carbonate (10.1 g, 73.2 mmol) and benzyl bromide (10.4 g, 61 mmol) were added. The reaction was heated at 60° C. for about 4 h. The reaction was filtered and the solid was washed with ethyl acetate. The filtrate was washed with water. The organic layers were washed with water and brine, dried and concentrated. The solid was recrystallized from acetone/hexane to give 14 g (90%) of 3-nitro-4-(benzyloxy)benzonitrile, as a white solid.

Workup

  1. additionwere added
  2. filtrationThe reaction was filtered
  3. washthe solid was washed with ethyl acetate
  4. washThe filtrate was washed with water
  5. washThe organic layers were washed with water and brine
  6. customdried
  7. concentrationconcentrated
  8. customThe solid was recrystallized from acetone/hexane

Sources & evidence

ORD record
ord-c864a34077284c93b501062812809166
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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