Bromine → 3-Fluoro-4-methoxyphenacyl bromide

HRID 10788

Reaction equation

HRID 10788 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Br:13]Br>O1CCOCC1>[Br:13][CH2:11][C:10]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=1)=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 968281-(3-Fluoro-4-methoxyphenyl)ethan-1-one

Product 1

HCID 70618463-Fluoro-4-methoxyphenacyl bromideYield 63%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 3′-fluoro-4′-methoxyacetophenone (1 g, 5.9 mmol) (Aldrich) in dioxane (10 mL) was added dropwise a solution of bromine (1.13 g, 7.1 mmol) in dioxane (30 mL). After stirring for 10 minutes, the mixture was concentrated in vacuo and the residue was purified by flash chromatography, with 10:4 hexanes/dichloromethane as an eluant, to provide 2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanone as a white powder (910 mg, 63% yield).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography, with 10:4 hexanes/dichloromethane as an eluant

Sources & evidence

ORD record
ord-a2a922a5821941fc85660d7e312d45ad
Source dataset
uspto-grants-2006_08
Patent number
US07094896B2

Linked notes

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