1-Chloro-4-(chloromethyl)benzene → 3-(3-Bromophenyl)-4-(4-chlorophenyl)-3-methyl-2-butanone

HRID 30358

반응식

HRID 30358 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:12])[C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.O.[OH-].[Cs+].C(OCC)(=O)C>C(Cl)Cl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:12])([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=2)[C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8857Ethyl AcetateHCID 23679066Caesium hydroxide--water (1/1/1)HCID 664367913-(3-Bromophenyl)butan-2-one

생성물 1

HCID 686756483-(3-Bromophenyl)-4-(4-chlorophenyl)-3-methyl-2-butanone

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-(3-bromophenyl)-2-butanone (2.0 g, 8.8 mmol) in methylene chloride (100 mL) was added 4-chlorobenzyl chloride (1.4 g, 8.8 mmol), tetrabutylammonium iodide (0.16 g, 0.44 mmol) and cesium hydroxide monohydrate (5.9 g, 35 mmol). After stirring at room temperature for 3.5 h, the reaction mixture was poured into ethyl acetate (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated to dryness to give the title compound. 1H NMR (400 MHz, CD3OD): δ 7.5-7.1 (m, 4 H), 7.08 (d, 2H), 6.68 (d, 2H), 3.16 (ABq, 2H), 1.98 (s, 3H), 1.42 (s, 3H).

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-b7583f5efae64ba4bc4392e03243ee37
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423067B2

연결된 노트

불러오는 중…