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

HRID 581871

Reaction equation

HRID 581871 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 54350482[3,4-Di(t-butyldimethylsilyloxymethyl)cyclopent-1-en-1-yl]methyl bromideYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b49f9aae8e3c476986544a3531c43585
Source dataset
uspto-grants-1999_07
Patent number
US05922727

Linked notes

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