Bromine → N-[4-(2-Bromoacetyl)Phenyl]Acetamide

HRID 23692

Reaction equation

HRID 23692 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([CH3:13])=[O:12])=[CH:6][CH:5]=1)=[O:3].[Br:14]Br>O1CCOCC1.C(OCC)C>[Br:14][CH2:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:12])[CH3:13])=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 75937N-(p-acetylphenyl)acetamide

Product 1

HCID 12364739N-[4-(2-Bromoacetyl)Phenyl]AcetamideYield 62.5%

Reagents, catalysts & solvents 1

HCID 23504442p-Dioxane ethyl etherSolvent

Procedure

To a suspension of 4-acetamidoacetophenone (Lancaster, 5.32 g, 0.03 mol) in 1,4-dioxane/diethyl ether (100 mL, 1:2, v/v) was added bromine (1.53 mL, 0.03 mol) via a syringe. The reaction mixture was stirred at room temperature for 4 hours until the color of the mixture was changed from brown to white. The solid was collected by filtration, washed with diethyl ether, and dried under high vacuum to give the title compound as a white solid (4.8 g).

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with diethyl ether
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-43e73a7d6a6541cb8fbdd66d015a07f5
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Linked notes

Loading…