Cesium carbonate → 2'-Chloro-5'-nitro-biphenyl-4-carboxylic acid ethyl ester

HRID 1678485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678485
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[Cl:11].[CH2:12]([O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)=[O:16])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[CH2:12]([O:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=2[Cl:11])=[CH:19][CH:18]=1)=[O:16])[CH3:13]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27343504-Ethoxycarbonylphenylboronic acidHCID 27355492-Bromo-1-chloro-4-nitrobenzene

Produkt 1

HCID 598223932'-Chloro-5'-nitro-biphenyl-4-carboxylic acid ethyl esterAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-1-chloro-4-nitro-benzene (2.5 g), 4-ethoxycarbonyl-phenyl boronic acid (2.05 g), cesium carbonate (3.44 g) and tetrakis(triphenylphosphine)palladium0 (catalytic quantity), in 1:2 aqueous DME (45 ml) was heated to reflux for 18 h. The mixture was then cooled and partitioned between water and ethyl acetate. The dried extracts were evaporated to give the product as a white solid (3.01 g). This material was used in the next stage without further purification.

Aufarbeitung

  1. temperatureto reflux for 18 h
  2. temperatureThe mixture was then cooled
  3. custompartitioned between water and ethyl acetate
  4. customThe dried extracts were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6977cb31729b42ff827e4ed78aace1e2
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008303B2

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