Carbon tetrabromide → 1-Bromo-9-octadecene

HRID 2393352Notes

Reaction equation

HRID 2393352 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-69c9a41993d1444ba1f7127159f119a3
Source dataset
uspto-grants-1998_09
Patent number
US05807862

Reaction notes

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