1-(2-Bromo-4-fluorophenyl)ethan-1-one → 2-Bromo-1-(2-bromo-4-fluorophenyl)ethanone

HRID 29264

Reaction equation

HRID 29264 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[Br-:12].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>O1CCCC1>[Br:12][CH2:10][C:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Br:1])=[O:11]

Participants

4

Reactant 2

HCID 27363041-(2-Bromo-4-fluorophenyl)ethan-1-oneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 218649482-Bromo-1-(2-bromo-4-fluorophenyl)ethanoneYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-(2-Bromo-4-fluoro-phenyl)-ethanone (2.5 g, 11.52 mmol) in anhydrous tetrahydrofuran (53 mL) under argon was added phenyltrimethylammonium tribromide (4.33 g, 11.52 mmol, 1.0 eq) at 0° C. The reaction mixture was stirred at ambient temperature for 16 h, concentrated, and re-dissolved in ethyl acetate. The organic layer was washed with water (2×150 mL) and brine (1×100 mL), dried (MgSO4), filtered, and evaporated in vacuo. Purification using MPLC chromatography (Biotage) gave 2.14 g (63%) of 2-bromo-1-(2-bromo-4-fluoro-phenyl)-ethanone as a clear oil. 1H-NMR (CD2Cl2) δ 7.57 (dd, J=9.6 Hz, 1H), 7.44 (dd, J=8, 2 Hz, 1H), 7.21 (m, 7.21-7.14, 1H), 4.51 (s, 2H); TLC Rf=0.38, 15% ethyl acetate-hexanes.

Workup

  1. concentrationconcentrated
  2. dissolutionre-dissolved in ethyl acetate
  3. washThe organic layer was washed with water (2×150 mL) and brine (1×100 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-56e3fb3e9d4345ee8837a0387bd56cf1
Source dataset
uspto-grants-2008_09
Patent number
US07420066B2

Linked notes

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