Sodium Iodide → 8-Iodooct-1-ene

HRID 1792409Notes

Reaction equation

HRID 1792409 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].[I-:10].[Na+]>CC(=O)CC>[I:10][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 759078-Bromooct-1-ene

Product 1

HCID 138898108-Iodooct-1-ene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 8-bromo-1-octene (1.34 g, 7 mmol) and sodium iodide (5.25 g, 35 mmol) in 2-butanone (15 ml) was stirred under reflux for 1 h. The mixture was concentrated in vacuo to a half of its original volume and hexane and water was added. Organic layer was washed with 5% aqueous sodium thiosulfate, saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate and concentrated in vacuum. Purification by flash chromatography on silica gel (hexane) gave 8-iodo-1-octene as colorless oil. yield: 1.54 g (92%).

Workup

  1. temperatureunder reflux for 1 h
  2. concentrationThe mixture was concentrated in vacuo to a half of its original volume and hexane and water
  3. additionwas added
  4. washOrganic layer was washed with 5% aqueous sodium thiosulfate, saturated sodium bicarbonate and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuum
  7. customPurification by flash chromatography on silica gel (hexane)

Sources & evidence

ORD record
ord-8f05e99b3c1f4ee294971c754d2bc47e
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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