Iodine → HCID 54202221, compound

HRID 1197178Notes

Reaction equation

HRID 1197178 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10][CH2:11]CC(O)=O)[CH:5]=[CH:6][CH:7]=1.[C:16](=[O:19])([O-])[OH:17].[K+].[I-:21].[K+].II.[C:25](=O)(O)[O-].[Na+]>C1COCC1.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:25][O:17][C:16](=[O:19])[CH:10]([CH2:11][I:21])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 807IodineHCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 516893Potassium BicarbonateHCID 54126933HCID 54126933, compound

Product 1

HCID 54202221HCID 54202221, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

6-(3-Bromophenyl)-5-hexenoic acid (1.0 g, 3.72 mmole) is dissolved in 15 ml THF in a 100 ml 2-neck round bottom flask under nitrogen. The solution is diluted with 7.5 ml water, treated with solid potassium hydrogen carbonate (430 mg, 4.3 mmole), and stirred 20 minutes at room temperature. The reaction mixture is protected from light, cooled to -20° C., and treated successively portion-wise with potassium iodide (2.7 g, 16.9 mmole) and iodine (8.5 g, 33.6 mmole). The reaction is stirred 30 minutes at -20° C. and warmed to room temperature to stir overnight. The reaction mixture is diluted with saturated sodium thiosulfate until colorless. The mixture is poured into 50 ml saturated sodium bicarbonate and extracted with 4×30 ml diethyl ether. The organics are combined, dried over magnesium sulfate, and concentrated in vacuo to a crude amber oil (1.5 g). The oil is chromatographed over 40 g silica gel (230-400 mesh), eluting with 25% acetone/hexane and collecting 9 ml fractions. Fractions 16-26 are combined and concentrated to give 1.3 g of the title compound as an amber solid. Following the above procedure gives the title compound having the physical characteristic described below:

Workup

  1. temperaturecooled to -20° C.
  2. stirringThe reaction is stirred 30 minutes at -20° C.
  3. temperaturewarmed to room temperature
  4. stirringto stir overnight
  5. extractionextracted with 4×30 ml diethyl ether
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo to a crude amber oil (1.5 g)
  8. customThe oil is chromatographed over 40 g silica gel (230-400 mesh)
  9. washeluting with 25% acetone/hexane
  10. customcollecting 9 ml fractions
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ce873b2dd7724fa09676225ca48bb34b
Source dataset
uspto-grants-1992_05
Patent number
US05116981

Reaction notes

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