Phosphorus tribromide → Farnesyl bromide

HRID 249123

Reaction equation

HRID 249123 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].CC(CCC=C(C)CCC=C(C)C)=CCN1C(=O)C2C(=CC=CC=2)C1=O.P(Br)(Br)[Br:44]>C(OCC)C>[CH2:2]([Br:44])[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

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 445070FarnesolHCID 542051882-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 550199Farnesyl bromide

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 1 (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 NaHC03, 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 NaHC03, 15 ml of H2O, and 15 ml of brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-8055d168db824518b0599ab852eb2409
Source dataset
uspto-grants-1993_05
Patent number
US05212164

Linked notes

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