Carbon tetrabromide → 1-(2-Bromoethyl)-2-cyclopropylbenzene

HRID 619804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619804
[C:1]1([C:7]2(CO)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P([C:25]2[CH:30]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>C1COCC1.CCOCC>[CH:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=2[CH2:25][CH2:30][Br:32])[CH2:8][CH2:9]1

Komponenten

6

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5205361-Phenylcyclopropanemethanol

Produkt 1

HCID 218459631-(2-Bromoethyl)-2-cyclopropylbenzeneAusbeute 64,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-phenyl-1-cyclopropane methanol (1 g, 6.8 mmol) in 35 mL of THF is added triphenylphosphine (1.7 g, 7.1 mmol) and carbon tetrabromide (2.34 g, 7.1 mmol). The solution is stirred at ambient temperatures for 5 hours. After this time, the solution is diluted with 100 mL of Et2O. The reaction mixture is filtered and the collected solution is concentrated. The crude product is purified by column chromatography eluting with hexane to afford the title compound (1 g, 4.4 mmol) as an oil.

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe collected solution is concentrated
  3. customThe crude product is purified by column chromatography
  4. washeluting with hexane

Quellen und Nachweise

ORD-Eintrag
ord-8df947c8f5aa4a79a1c8da12622388e1
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958918

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