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

HRID 353725Notes

Reaction equation

HRID 353725 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-a631004e51534d27802d64ea12a71f85
Source dataset
uspto-grants-2004_06
Patent number
US06756374B2

Reaction notes

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