a Farnesol → Farnesyl bromide

HRID 861711Notes

Reaction equation

HRID 861711 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(=O)([O-])[O-].[Na+].[Na+]>C(OC(C)C)(C)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

5

Reactant 3

HCID 3327a Farnesol2×HCID 10340Sodium CarbonateHCID 24614Phosphorus tribromide

Product 1

HCID 550199Farnesyl bromideYield 224.9%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
-20 °C

Procedure

Into an argon-replaced 1 liter reaction vessel, 66.6 g (0.3 mol) of farnesol (all trans-form) was charged, and 300 ml of isopropyl ether was further added to dissolve farnesol. The resulting solution was cooled to -20° C., and thereafter 32.5 g (0.12 mol) of phosphorus tribromide was added to carry out reaction at -20° C. to -10° C. for 2 hours. The reaction mixture thus obtained was poured into 400 ml of an aqueous 5% sodium carbonate solution, and the liquid was separated. The organic layer was washed with saturated brine, followed by distillation of the solvent to obtain 77.0 g of farnesyl bromide (yield: 90%). Data of physical properties of this compound are shown below.

Workup

  1. additionwas charged
  2. customreaction at -20° C. to -10° C. for 2 hours
  3. customThe reaction mixture thus obtained
  4. customthe liquid was separated
  5. washThe organic layer was washed with saturated brine
  6. distillationfollowed by distillation of the solvent

Sources & evidence

ORD record
ord-3be3b48818744e09932ef8afd4922f7c
Source dataset
uspto-grants-1998_02
Patent number
US05714645

Reaction notes

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