Benzyl Bromide → 1-Acetamido-4-benzyloxy-2-nitrobenzene

HRID 1414772Notes

Reaction equation

HRID 1414772 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:2].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 4024832N-(4-hydroxy-2-nitrophenyl)acetamide

Product 1

HCID 2658881-Acetamido-4-benzyloxy-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.94 G. of 1-acetamido-4-hydroxy-2-nitrobenzene, 5.13 g. of benzyl bromide and 4.2 g. anhydrous potassium carbonate are refluxed overnight in acetone with stirring, evaporated to dryness, the excess benzyl bromide removed under vacuum, water added and the product extracted with dichloromethane to give 1-acetamido-4-benzyloxy-2-nitrobenzene.

Workup

  1. customevaporated to dryness
  2. customthe excess benzyl bromide removed under vacuum, water
  3. additionadded
  4. extractionthe product extracted with dichloromethane

Sources & evidence

ORD record
ord-ce06c513fcf0480d8862c83d43707fb2
Source dataset
uspto-grants-1977_01
Patent number
US04002640

Reaction notes

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