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

HRID 30358

Reaktionsgleichung

Reaktionsgleichung von HRID 30358
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b7583f5efae64ba4bc4392e03243ee37
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423067B2

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