Carbon tetrabromide → [3,4-Di(t-butyldimethylsilyloxymethyl)cyclopent-1-en-1-yl]methyl bromide

HRID 581871

Reaktionsgleichung

Reaktionsgleichung von HRID 581871
[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[CH:38]([CH2:39][O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH2:37][C:36](CO)=[CH:35]1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>ClCCl>[Si:25]([O:32][CH2:33][CH:34]1[CH:38]([CH2:39][O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:42])[CH3:43])[CH2:37][C:36]([CH2:1][Br:5])=[CH:35]1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67554500[3,4-Di(t-butyldimethylsilyloxymethyl)cyclopent-1-en-1-yl]methyl alcohol

Produkt 1

HCID 54350482[3,4-Di(t-butyldimethylsilyloxymethyl)cyclopent-1-en-1-yl]methyl bromideAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of carbon tetrabromide (3.18 g, 9.6 mmol) and triphenyl phosphine (3.15 g, 12.9 mmol) were added to [3,4-di(t-butyldimethylsilyloxymethyl)cyclopent-1-en-1-yl]methyl alcohol (3.09 g, 8.0 mmol) in dichloromethane under ice bath and then, the reaction mixture was stirred for 30 min at 0° C. After overnight at room temperature, the reaction mixture was extracted with dichloromethane, dried with MgSO4, filtered, concentrated and separated by column chromatography to give a desirable product (2.43 g).

Aufarbeitung

  1. waitAfter overnight at room temperature
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customseparated by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b49f9aae8e3c476986544a3531c43585
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922727

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