Carbon tetrabromide → (4-t-Butyldimethylsilyloxymethylcyclopent-1-en-1-yl)methyl bromide

HRID 581853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 581853
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Si:25]([O:32][CH2:33][CH:34]1[CH2:38][C:37](CO)=[CH:36][CH2:35]1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>ClCCl>[Si:25]([O:32][CH2:33][CH:34]1[CH2:35][C:36]([CH2:1][Br:5])=[CH:37][CH2:38]1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54331641HCID 54331641, Verbindung

Produkt 1

HCID 53841289(4-t-Butyldimethylsilyloxymethylcyclopent-1-en-1-yl)methyl bromideAusbeute 49,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The carbon tetrabromide (1.39 g, 4.2 mmol) and triphenylphosphine (1.37 g, 5.2 mmol) were added in dichloromethane solution of (4-t-Butyldimethylsilyloxymethylcyclopent-1-en-1-yl)methyl alcohol (0.85 g, 3.5 mmol) under ice bath and then stirred for 30 min at 0° C. The reaction mixture was stirred for overnight at room temperature, extracted with dichloromethane, dried with MgSO4, filtered, concentrated and separated by column chromatography to give a desirable product (0.53 g).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for overnight at room temperature
  2. extractionextracted with dichloromethane
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customseparated by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7fcaf4c39ee6443d9c0689cf8525c585
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922727

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