1-(2-Chlorophenyl)-2-(4-chlorophenyl)ethanone → 2-Bromo-1-(2-chlorophenyl)-2-(4-chlorophenyl)ethanone

HRID 1436160Notes

Reaction equation

HRID 1436160 reaction equation
[Br-:1].[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.[Cl:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41](=[O:50])[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][CH:44]=1>C1COCC1.ClCCl>[Br:1][CH:42]([C:43]1[CH:44]=[CH:45][C:46]([Cl:49])=[CH:47][CH:48]=1)[C:41]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[Cl:34])=[O:50]

Participants

5

Reactant 2

HCID 3483121-(2-Chlorophenyl)-2-(4-chlorophenyl)ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 177481382-Bromo-1-(2-chlorophenyl)-2-(4-chlorophenyl)ethanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

29.54 g of phenyltrimethylammonium tribromide are added to a solution of 20.83 g of 1-(2-chlorophenyl)-2-(4-chlorophenyl)ethanone in THF. The homogeneous solution is stirred at room temperature for 1 hour 15 minutes. The reaction medium is filtered and concentrated to dryness. The crude reaction product is taken up in dichloromethane and washed successively with water, with aqueous Na2CO3 solution and then with water. The organic phase is dried over Na2SO4, filtered and concentrated to dryness by distilling off the solvent under reduced pressure. The product is obtained in the form of an oil that crystallizes slowly. The crystals are washed with a minimum amount of ethanol to give the expected product.

Workup

  1. filtrationThe reaction medium is filtered
  2. concentrationconcentrated to dryness
  3. customThe crude reaction product
  4. washwashed successively with water, with aqueous Na2CO3 solution
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. distillationby distilling off the solvent under reduced pressure
  9. customThe product is obtained in the form of an oil
  10. customthat crystallizes slowly
  11. washThe crystals are washed with a minimum amount of ethanol

Sources & evidence

ORD record
ord-c5d7157c024e456fb8a3d99fec778240
Source dataset
uspto-grants-2009_11
Patent number
US07618991B2

Reaction notes

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