Benzyl Bromide → HCID 22010922, compound

HRID 323131Notes

Reaction equation

HRID 323131 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:20])[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O>[CH2:27]([O:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:20])[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5697817HCID 5697817, compound

Product 1

HCID 22010922HCID 22010922, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-hydroxy-4-methylphenyl)-4-nitrobenzamide (3.8 g) in N,N-dimethylformamide (25 ml) was added potassium carbonate (3.85 g) and benzyl bromide (2.63 g). The reaction mixture was stirred at ambient temperature for 3 hours. The mixture was extracted with ethyl acetate and washed with water and brine. The organic solution was dried over magnesium sulfate. The solvent was removed by evaporation to give N-(2-benzyloxy-4-methylphenyl)-4-nitrobenzamide (4.8 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialThe organic solution was dried over magnesium sulfate
  4. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-3ee2717eab3d408592b5a9425fc04c54
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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