Carbon tetrabromide → 1-(2-Bromoethyl)-4-chloro-2-nitrobenzene

HRID 1743869Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743869
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>C(Cl)Cl>[Br:34][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[N+:11]([O-:13])=[O:12]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 144915122-(4-Chloro-2-nitrophenyl)ethanol

Produkt 1

HCID 222365841-(2-Bromoethyl)-4-chloro-2-nitrobenzeneAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(4-chloro-2-nitro-phenyl)-ethanol (63.0 g, 0.31 mole) in methylene chloride (1 L) was added triphenylphosphine (81.9 g, 0.31 mole) and the mixture was cooled to 0° C. Carbon tetrabromide (103.6 g, 0.31 mole) in methylene chloride (100 mL) was added dropwise through an addition funnel. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue purified by flash column chromatography (silica gel, dichloromethane) to provide 78.0 g of the title compound as a light brown oil.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash column chromatography (silica gel, dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-a5030b5bbd79498c8c33d8fe7c249935
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012089B2

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