Carbon tetrabromide → 1-Bromo-9-octadecene

HRID 1637663

Reaction equation

HRID 1637663 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20](O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C(Br)(Br)(Br)[Br:40]>ClCCl>[Br:40][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=[CH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5284499Oleyl Alcohol

Product 1

HCID 802021-Bromo-9-octadeceneYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This example is a method of synthesis for inventive compound no. 3508. Triphenylphosphine (5.24 g, 20 mmol) was added incrementally to a solution of oleyl alcohol (5.37 g, 20 mmol) and carbontetrabromide (6.63 g, 20 mmol) in 400 ml of dichloromethane, the resulting reaction mixture being stirred for an hour at room temperature. Removing the solvent under reduced pressure, left a residue, which was extracted with three 200 ml aliquots of hexane. Further purification by flash chromatography over silica gel using a hexane eluant produced 5.82 g of 1-bromo-9-octadecene (88% yield).

Workup

  1. customa method of synthesis for inventive compound no
  2. customthe resulting reaction mixture
  3. customRemoving the solvent under reduced pressure
  4. waitleft a residue, which
  5. extractionwas extracted with three 200 ml aliquots of hexane
  6. customFurther purification by flash chromatography over silica gel using a hexane eluant

Sources & evidence

ORD record
ord-bbd4d39c884248b187c943360b41204e
Source dataset
uspto-grants-2000_03
Patent number
US06043250

Linked notes

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