Bromine → 2-Bromo-1-(3-bromo-4-methylphenyl)ethanone

HRID 1619149Notes

Reaction equation

HRID 1619149 reaction equation
[Br:1]Br.[Br:3][C:4]1[CH:5]=[C:6]([C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][C:9]=1[CH3:10]>C(Cl)(Cl)Cl>[Br:1][CH2:12][C:11]([C:6]1[CH:7]=[CH:8][C:9]([CH3:10])=[C:4]([Br:3])[CH:5]=1)=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 33094011-(3-Bromo-4-methylphenyl)ethan-1-one

Product 1

HCID 126224992-Bromo-1-(3-bromo-4-methylphenyl)ethanoneYield 105.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of bromine (0.68 mL, 13.3 mmol) in chloroform (13 mL) was added dropwise over a 35 minute period to a stirred solution of 1-(3-bromo-4-methylphenyl)ethanone (2.96 g, 13.9 mmol) in chloroform (40 mL) at 0° C. After the addition, the ice-bath was removed and the mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure to give an oil which crystallized to give the title compound (4.11 g, 95%) as an orange solid.

Workup

  1. additionAfter the addition
  2. customthe ice-bath was removed
  3. customThe solvent was removed under reduced pressure
  4. customto give an oil which
  5. customcrystallized

Sources & evidence

ORD record
ord-bd7aea0441774ac8a6d3c5e271cd2f8d
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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