Bromine → 2-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-one

HRID 1429199Notes

Reaction equation

HRID 1429199 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Br:14]Br>C1C=CC=CC=1>[Br:14][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)=[O:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 795964'-Chloro-3'-nitroacetophenone

Product 1

HCID 27783302-Bromo-1-(4-chloro-3-nitrophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a 500 mL round-bottomed flask was added 1-(4-chloro-3-nitrophenyl)ethanone (11.98 g, 60 mmol) in benzene (75 mL) to give a white suspension. Bromine (9.59 g, 60.0 mmol) was added dropwise over 5 minutes to give a deep red solution. The mixture was stirred for 1 hour to give a yellow solution that was concentrated in vacuo to a yellow solid. Recrystallized from 9:1 hexane/ethyl acetate gave 2-bromo-1-(4-chloro-3-nitrophenyl)ethanone as yellow needles.

Workup

  1. customto give a white suspension
  2. customto give a deep red solution
  3. customto give a yellow solution that
  4. concentrationwas concentrated in vacuo to a yellow solid
  5. customRecrystallized from 9:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-b67ee5469e014a8b8ec5129d1bb9b06f
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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