Carbon tetrabromide → 2-(5-Methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl bromide

HRID 963706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 963706
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:13][CH2:14]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:35]C(Br)(Br)Br>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH:8]2[CH2:13][CH2:14][Br:35]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 106083702-(5-Methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethanol

Produkt 1

HCID 105638762-(5-Methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl bromideAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a solution of 2-(5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethanol (0.20 g) and triphenylphosphine (0.42 g) in dichloromethane (10 ml) was added tetrabromomethane (0.90 g) at 5° C. The solution was stirred at 5° C. for 1.5 hours and evaporated in vacuo. To the residue, ethyl acetate was added and the insoluble material was filtered off. The ethyl acetate solution was evaporated in vacuo. The residue was chromatographed (n-hexane) over silica gel to afford 2-(5-methoxy-1,2,3,4-tetrahydro-1-naphthyl)ethyl bromide (0.18 g) as a colorless oil.

Aufarbeitung

  1. customevaporated in vacuo
  2. additionTo the residue, ethyl acetate was added
  3. filtrationthe insoluble material was filtered off
  4. customThe ethyl acetate solution was evaporated in vacuo
  5. customThe residue was chromatographed (n-hexane) over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b6211b5f490e4c9ca781cb8cf8edf7e1
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763489

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