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

HRID 982717Notes

Reaction equation

HRID 982717 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-7e3dab8921854442b94056fa4e3df42d
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

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