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

HRID 10786

Reaction equation

HRID 10786 reaction equation
[Br:1]Br.[C:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)(=[O:5])[CH3:4].C(O)(=O)C>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:4][C:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 75937N-(p-acetylphenyl)acetamide

Product 1

HCID 12364739N-[4-(2-Bromoacetyl)Phenyl]AcetamideYield 97.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of bromine (0.31 mL, 5.9 mmol) in carbon tetrachloride (10 mL) was added to a suspension of N-(4-acetylphenyl)acetamide (1 g, 5.6 mmol) (Lancaster Synthesis) in carbon tetrachloride (20 mL). The reaction mixture was stirred for several hours but TLC indicated only starting material. Acetic acid (10 mL) was added, and the reaction mixture was stirred overnight. Filtration gave N-[4-(bromoacetyl)phenyl]acetamide (1.4 g) as a solid. HPLC indicated that the purity was approximately 80%. This material was used directly in subsequent steps without purification.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. filtrationFiltration

Sources & evidence

ORD record
ord-f5d11cfe3cd8412daee3285f06654237
Source dataset
uspto-grants-2006_08
Patent number
US07094896B2

Linked notes

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