Phosphorus tribromide → Neryl bromide

HRID 918559Notes

Reaction equation

HRID 918559 reaction equation
[CH3:1]/[C:2](/[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])=[CH:3]/[CH2:4]O.P(Br)(Br)[Br:13]>C(OCC)C>[Br:13][CH2:4]/[CH:3]=[C:2](/[CH3:1])\[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 643820Nerol

Product 1

HCID 6087681Neryl bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of 51.4 grams of (Z)-3,7-dimethyl-2,6-octadien-1-ol in 400 milliliters of dry ethyl ether, protected from light, is treated with 29.8 grams of phosphorous tribromide, dropwise, over a 1/2 hour period. The mixture is refluxed for about 2.5 hours, then cooled, poured on ice water and extracted with ether. The ethereal extract is washed with sodium bicarbonate, then with water and dried over sodium sulfate. Solvent is removed under reduced pressure to yield (Z)-1-bromo-3,7-dimethyl-2,6-octadiene.

Workup

  1. temperatureThe mixture is refluxed for about 2.5 hours
  2. temperaturecooled
  3. additionpoured on ice water
  4. extractionextracted with ether
  5. extractionThe ethereal extract
  6. washis washed with sodium bicarbonate
  7. dry with materialwith water and dried over sodium sulfate
  8. customSolvent is removed under reduced pressure

Sources & evidence

ORD record
ord-9905993297714bbcaf9563f7ddf7254b
Source dataset
uspto-grants-1976_07
Patent number
US03971827

Reaction notes

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