3-Chlorobiphenyl → 1-Bromo-2-(3'-chlorobiphenyl-4-yl)ethanone

HRID 1593663

Reaktionsgleichung

Reaktionsgleichung von HRID 1593663
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:15][C:16]([Br:18])=[O:17].[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[Br:18][C:16](=[O:17])[CH2:15][C:11]1[CH:10]=[CH:9][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 163223-ChlorobiphenylHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 223354751-Bromo-2-(3'-chlorobiphenyl-4-yl)ethanoneAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

A mixture of 5 g (0.026 mole) of 3-chlorobiphenyl, 50 ml of methylene chloride, 6.95 g (0.034 mole) of bromoacetyl bromide is cooled to 0-5° C. and 4 g (0.030 mole) of aluminum trichloride are added. The mixture is stirred for 1 hour at 5° C., then for 4 hours at room temperature. It is poured onto an ice/water mixture, extracted with methylene chloride, the organic phase is washed with a 1N solution of HCl, dried over sodium sulfate and evaporated under reduced pressure. 4.5 g of the title product is obtained. M.p. 63-65° C.

Aufarbeitung

  1. waitfor 4 hours at room temperature
  2. extractionextracted with methylene chloride
  3. washthe organic phase is washed with a 1N solution of HCl
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4e7e304ed497409aacff5818a794cb75
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297799B2

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