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

HRID 30358

反応式

HRID 30358 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b7583f5efae64ba4bc4392e03243ee37
出典データセット
uspto-grants-2008_09
特許番号
US07423067B2

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