Bromine → 3-Fluoro-4-methoxyphenacyl bromide

HRID 2415275Notes

Reaction equation

HRID 2415275 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 mmmol) (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 (91,0 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-2b0295ea5c984414aedb3f4c13c34bb6
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

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