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

HRID 83852ノート

反応式

HRID 83852 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cca09b6e7ed24b81b5297e2d3ef6eb2a
出典データセット
uspto-grants-2014_09
特許番号
US08846739B2

反応ノート

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