3-(3,4-Dichlorophenyl)-3-methylbutan-2-one → 1-Bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-one

HRID 83852Notes

Reaction equation

HRID 83852 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:55][C:56]1[CH:57]=[C:58]([C:63]([CH3:68])([CH3:67])[C:64](=[O:66])[CH3:65])[CH:59]=[CH:60][C:61]=1[Cl:62]>CO.C(Cl)Cl>[Br:1][CH2:65][C:64](=[O:66])[C:63]([C:58]1[CH:59]=[CH:60][C:61]([Cl:62])=[C:56]([Cl:55])[CH:57]=1)([CH3:68])[CH3:67]

Participants

4

Reactant 2

HCID 212584633-(3,4-Dichlorophenyl)-3-methylbutan-2-oneHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 212583981-Bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-oneYield 91.7%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Tetrabutylammonium tribromide (20.4 g, 41.5 mmol) was added to a solution of 3-(3,4-dichlorophenyl)-3-methylbutan-2-one (9.60 g, 41.5 mmol) in MeOH-DCM (160 mL, 1:2, v/v). After stirring 24 h, the reaction mixture was concentrated under reduced pressure and then combined with EtOAc (80 mL). The organic layer was washed with H2O (50 mL), 1N HCl (50 mL), and H2O (20 mL) successively. The organic layer was washed with brine, dried over Na2SO4, and concentrated. Purification by column chromatography afforded 1-bromo-3-(3,4-dichlorophenyl)-3-methylbutan-2-one (11.8 g, 91%). 1H NMR (400 MHz, CDCl3) δ 7.45 (d, 1H), 7.38 (d, 1H), 7.08 (d, 1H), 3.86 (s, 2H), 1.56 (s, 6H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. washThe organic layer was washed with H2O (50 mL), 1N HCl (50 mL), and H2O (20 mL) successively
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-cca09b6e7ed24b81b5297e2d3ef6eb2a
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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