Carbon tetrabromide → (5-t-Butyldimethylsilyloxymethylcyclopent-1-en-1-yl)methyl bromide

HRID 581858Notes

Reaction equation

HRID 581858 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[C:38](CO)=[CH:37][CH2:36][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[C:35]([CH2:1][Br:5])=[CH:36][CH2:37][CH2:38]1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54371071(5-t-Butyldimethylsilyloxymethylcyclopent-1-en-1-yl)methyl alcohol

Product 1

HCID 53795506(5-t-Butyldimethylsilyloxymethylcyclopent-1-en-1-yl)methyl bromideYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The carbon tetrabromide (8.5 g, 25.7 mmol) and triphenylphosphine (8.4 g, 3.22 mmol) were added in dichloromethane solution of (5-t-Butyldimethylsilyloxymethylcyclopent-1-en-1-yl)methyl alcohol (5.2 g, 21.4 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 (3.08 g).

Workup

  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

Sources & evidence

ORD record
ord-94f5d44e51d24a1cb5779a70572a34e8
Source dataset
uspto-grants-1999_07
Patent number
US05922727

Reaction notes

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