Diethyl Ether → 1-Bromo-6-methylundec-2-yn-5-ene

HRID 1606675Notes

Reaction equation

HRID 1606675 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:3][CH2:4][C:5]#[C:6][CH2:7]O.CCOCC.P(Br)(Br)[Br:20]>N1C=CC=CC=1>[Br:20][CH2:7][C:6]#[C:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 544358746-Methylundec-2-yn-5-en-1-ol

Product 1

HCID 540103301-Bromo-6-methylundec-2-yn-5-ene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 17 g. of 6-methylundec-2-yn-5-en-1-ol, 32.4 ml. of ether, and 2.07 ml. of pyridine was stirred under nitrogen in an ice-salt bath and 4.5 ml. of phosphorus tribromide was added. The ice-salt bath was then removed and the mixture was first allowed to warm to room temperature, then was heated under reflux for 2.5 hrs. The mixture was again cooled in an ice bath, and 15 ml. each of ether and water were added. The ether layer was separated, washed with aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried over sodium sulfate, and evaporated. The thus obtained residue was distilled, collecting 14 g. of a mixture comprising 1-bromo-6-methylundec-2-yn-5-ene at 85°-89°C./0.005 mm.

Workup

  1. additionA mixture of 17 g
  2. customThe ice-salt bath was then removed
  3. temperaturewas heated
  4. temperatureunder reflux for 2.5 hrs
  5. temperatureThe mixture was again cooled in an ice bath
  6. additioneach of ether and water were added
  7. customThe ether layer was separated
  8. washwashed with aqueous sodium bicarbonate, saturated aqueous sodium chloride
  9. dry with materialdried over sodium sulfate
  10. customevaporated
  11. distillationThe thus obtained residue was distilled
  12. customcollecting 14 g
  13. customat 85°-89°C.

Sources & evidence

ORD record
ord-993d5f4895e74349b83ad689defa3c95
Source dataset
uspto-grants-1976_04
Patent number
US03953499

Reaction notes

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