Water → 2,6-Difluorophenacyl bromide

HRID 1962548Notes

Reaction equation

HRID 1962548 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9](=[O:11])[CH3:10].[Cl-].[Al+3].[Cl-].[Cl-].[Br:16]Br.O>C(OCC)C>[Br:16][CH2:10][C:9]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 836431-(2,6-Difluorophenyl)ethan-1-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27782632,6-Difluorophenacyl bromideYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-(2,6-difluorophenyl)ethanone (10.0 g) in diethyl ether (50 mL) was added anhydrous aluminum chloride (86 mg) and the mixture was stirred for 5 min. Bromine (3.3 mL) was added dropwise at 10-15° C. After stirring at room temperature for 2 hr, the mixture was poured into water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure to give the title compound as a pale-yellow oil (yield 15.2 g, about 100%).

Workup

  1. stirringAfter stirring at room temperature for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c2c3aa9a2724e879d8de3dc621b792c
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Reaction notes

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