Water → HCID 21919361, compound

HRID 1244430Notes

Reaction equation

HRID 1244430 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](I)[CH:5]=[CH:6][CH:7]=1.C(=O)(O)[O-].[Na+].[CH2:14]([OH:18])[CH:15]=[CH:16][CH3:17].O>CN1CCCC1=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]([CH3:17])[CH2:15][CH:14]=[O:18])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 122691-Chloro-3-iodobenzeneHCID 200242-Buten-1-olHCID 516892Sodium Bicarbonate

Product 1

HCID 21919361HCID 21919361, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-chloroiodobenzene (2.38 g), palladium acetate (20 mg), sodium bicarbonate (1.01 g) and crotyl alcohol (1.28 ml) in N-methylpyrrolidone (4 ml) was stirred and heated at 130° C. for 2 hours. The reaction mixture was allowed to cool, water (50 ml) was added and the mixture was extracted with diethyl ether (2×50 ml). The combined organic extracts were dried and the residue obtained on removal of the solvent was purified by chromatography through silica eluting with a mixture of ethyl acetate and methylene chloride (1:20) to give the title compound as an oil, yield 519 mg, M−H=181

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with diethyl ether (2×50 ml)
  3. customThe combined organic extracts were dried
  4. customthe residue obtained on removal of the solvent
  5. customwas purified by chromatography through silica eluting with a mixture of ethyl acetate and methylene chloride (1:20)

Sources & evidence

ORD record
ord-00d408c6430743c2b9b58e4047800cd7
Source dataset
uspto-grants-2006_10
Patent number
US07122551B2

Reaction notes

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