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

HRID 344039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 344039
[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-3251c7b1e6d043a999c253b377ccbdf9
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05863918

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