10-Undecen-1-ol → 11-Bromo-1-undecene

HRID 537388Notes

Reaction equation

HRID 537388 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].P(Br)(Br)[Br:14]>C1(C)C=CC=CC=1>[Br:14][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

4

Reactant 2

HCID 818510-Undecen-1-olHCID 24614Phosphorus tribromide

Product 1

HCID 28414811-Bromo-1-undecene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A five liter reaction flask was fitted with a mechanical stirring apparatus, a condenser, an addition funnel, and a thermocouple. The reaction flask was flame dried, and then cooled under a nitrogen atmosphere to room temperature. Under a static nitrogen blanket the reaction flask was charged with 10-undecen-1-ol (468 g, 3 mol) and toluene (1 L) while stirring. The contents were cooled to −10° C. and phosphorus tribromide (270 g, 1 mol) was added dropwise. The temperature was maintained at −10° C. with the aid of a Jack-o-matic, and the reaction mixture was aged for one hour. The reaction mixture was subsequently quenched and washed with brine (1 L). The organic layer was removed, and the product was distilled to provide 11-bromo-undec-1-ene (boiling point 95° C. at a pressure of 10 mm Hg).

Workup

  1. customA five liter reaction flask
  2. customwas fitted with a mechanical stirring apparatus, a condenser, an addition funnel
  3. temperatureThe reaction flask was flame
  4. customdried
  5. temperatureThe contents were cooled to −10° C.
  6. temperatureThe temperature was maintained at −10° C. with the aid of a Jack-o-matic
  7. customThe reaction mixture was subsequently quenched
  8. washwashed with brine (1 L)
  9. customThe organic layer was removed
  10. distillationthe product was distilled

Sources & evidence

ORD record
ord-324853ad10684c84a914799a6c01ed6f
Source dataset
uspto-grants-2014_10
Patent number
US08859820B1

Reaction notes

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