Phosphorus tribromide → Farnesyl bromide

HRID 327900Notes

Reaction equation

HRID 327900 reaction equation
O[CH2:2]/[CH:3]=[C:4](/[CH2:6][CH2:7]/[CH:8]=[C:9](/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])\[CH3:10])\[CH3:5].P(Br)(Br)[Br:18]>C(OCC)C>[CH2:2]([Br:18])[CH:3]=[C:4]([CH2:6][CH2:7][CH:8]=[C:9]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH3:10])[CH3:5]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 445070Farnesol

Product 1

HCID 550199Farnesyl bromideYield 216.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2.00 g (9.0 mmol) of (E,E)-farnesol in 20 ml of dry diethyl ether at 0° C. under argon in the dark was treated dropwise with a solution of 735 μl (4.0 mmol, 0.45 eq.) of PBr3 in 4 ml of dry diethyl ether. The resultant mixture was stirred at 0° C. for one hour, then quenched with H2O and separated. The organic phase was washed with 15 ml of NaHCO3, 15 ml of H2O, and 15 ml of brine, dried over MgSO4 and evaporated to provide 2.47 g of crude farnesyl bromide as a clear oil.

Workup

  1. customquenched with H2O
  2. customseparated
  3. washThe organic phase was washed with 15 ml of NaHCO3, 15 ml of H2O, and 15 ml of brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-ad4f84ebab8644808c03e7fb1d1507fe
Source dataset
uspto-grants-1993_12
Patent number
US05273969

Reaction notes

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