Bromine → 2'-Fluoro-4'-iodophenacyl bromide

HRID 561963Notes

Reaction equation

HRID 561963 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[C:11](=[O:13])[CH3:12]>C(O)(=O)C>[Br:1][CH2:12][C:11]([C:5]1[CH:6]=[CH:7][C:8]([I:10])=[CH:9][C:4]=1[F:3])=[O:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 534154542'-Fluoro-4'-iodoacetophenone

Product 1

HCID 872327682'-Fluoro-4'-iodophenacyl bromideYield 99.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (2.74 mL, 53.18 mmol) in acetic acid (30 mL) was added dropwise to a solution of 1-(2-fluoro-4-iodo-phenyl)-ethanone (14.04 g, 53.18 mmol) in acetic acid (200 mL) at room temperature under an atmosphere of nitrogen and then stirred for 24 hours. The reaction was concentrated to near dryness in vacuo, diluted with ethyl acetate (200 mL) and basified with saturated aqueous sodium carbonate solution. The organic layer was washed with brine, dried over sodium sulfate, filtered through a pad of silica gel and concentrated in vacuo to give 2-bromo-1-(2-fluoro-4-iodo-phenyl)-ethanone (18.10 g, 99%).

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with ethyl acetate (200 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered through a pad of silica gel
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4717d0ca9600477c806380aa438c14b3
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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