Hexane → 2-Bromo-1-(4-chloro-3-fluorophenyl)ethanone

HRID 1436449Notes

Reaction equation

HRID 1436449 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[F:11].[Br-:12].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC.C(OCC)(=O)C>C(Cl)Cl.CO>[Br:12][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:11])[CH:4]=1)=[O:10]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 38220774'-Chloro-3'-fluoroacetophenoneHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 230032952-Bromo-1-(4-chloro-3-fluorophenyl)ethanoneYield 69%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 1-(4-chloro-3-fluorophenyl)ethanone (3.4 g, 19.7 mmol), prepared in the previous step, in methylene chloride:methanol (1:3) was added tetrabutylammonium tribromide (9.5 g, 19.7 mmol) in portions. The reaction was monitored by TLC (3:1 hexane:ethyl acetate) until the starting material was consumed. The reaction solution was concentrated in vacuo and the residue was partitioned between diethyl ether and water. The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 4.2 g of crude product. The crude product was purified on silica gel using 5% ethyl acetate:hexane to give 2-bromo-1-(4-chloro-3-fluoro-phenyl)-ethanone (3.4 g, 69%) as desired product, MS (ES) m/z 252 [M+H+].

Workup

  1. customwas consumed
  2. concentrationThe reaction solution was concentrated in vacuo
  3. customthe residue was partitioned between diethyl ether and water
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give 4.2 g of crude product
  9. customThe crude product was purified on silica gel using 5% ethyl acetate

Sources & evidence

ORD record
ord-5080b2c6a2f24bc08863019aeb39f773
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

Loading…