Chloroacetyl chloride → N-(4-bromo-2-nitrophenyl)-2-chloroacetamide

HRID 44185

Reaction equation

HRID 44185 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[Cl:12][CH2:13][C:14](Cl)=[O:15]>>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14](=[O:15])[CH2:13][Cl:12])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 701324-Bromo-2-nitroaniline

Product 1

HCID 16457083N-(4-bromo-2-nitrophenyl)-2-chloroacetamideYield 96%

Procedure

To a solution of 4-bromo-2-nitroaniline (15.0 g, 69.1 mmol) was added drop wise 2-chloroacetyl chloride (9.4 g, 82.9 mmol) under nitrogen. After refluxing for 1.5 h, the reaction mixture was cooled to ambient temperature and the solvent was removed under reduced pressure. Crystallization from ethyl acetate/hexane afforded N-(4-bromo-2-nitrophenyl)-2-chloroacetamide (19.4 g, 66.1 mmol, 96%) as yellow needles.

Workup

  1. temperatureAfter refluxing for 1.5 h
  2. customthe solvent was removed under reduced pressure
  3. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ffe1c224bf7a4abdb0904482ad6ae5ce
Source dataset
uspto-grants-2013_09
Patent number
US08541404B2

Linked notes

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