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

HRID 83852노트

반응식

HRID 83852 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cca09b6e7ed24b81b5297e2d3ef6eb2a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846739B2

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