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

HRID 1679452Notes

Reaction equation

HRID 1679452 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-2d3d477b1bc347948b247694f93c8bb0
Source dataset
uspto-grants-1978_03
Patent number
US04080461

Reaction notes

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