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

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

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 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

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

Sources & evidence

ORD record: ord-ffe1c224bf7a4abdb0904482ad6ae5ce
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541404B2

Reaction notes

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