Bromine → 2-Bromo-1-(3,5-difluorophenyl)ethanone

HRID 2213894Notes

Reaction equation

HRID 2213894 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[Br:12]Br>O1CCOCC1>[Br:12][CH2:10][C:9]([C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=1)=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 5185963',5'-Difluoroacetophenone

Product 1

HCID 27783312-Bromo-1-(3,5-difluorophenyl)ethanoneYield 64.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 3′,5′-difluoroacetophenone (3 g, 19.2 mmol) (Lancaster Synthesis) in dioxane (30 mL) was added dropwise a solution of bromine (3.67 g, 23 mmol) in dioxane (75 mL). After stirring for 10 minutes, the mixture was concentrated in vacuo and the residue was purified by flash chromatography, with 10:2 hexanes/dichloromethane as an eluant, to provide 2-bromo-1-(3,5-difluorophenyl)ethanone as a colorless oil (2.9 g, 64% yield).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography, with 10:2 hexanes/dichloromethane as an eluant

Sources & evidence

ORD record
ord-cdfdef676f3f4d5091076816899cb834
Source dataset
uspto-grants-2006_09
Patent number
US07105670B2

Reaction notes

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