Phosphate → 1-(Cyclopentylthio)-3-iodo-5-methylbenzene

HRID 2118342Notes

Reaction equation

HRID 2118342 reaction equation
I[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([I:9])[CH:3]=1.C(N(CC)CC)C.[CH:17]1([SH:22])[CH2:21][CH2:20][CH2:19][CH2:18]1.P([O-])([O-])([O-])=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O.CN1CCCC1=O>[CH:17]1([S:22][C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([I:9])[CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

9

Reactant 4

HCID 1061PhosphateHCID 8471TriethylamineHCID 15510CyclopentanethiolHCID 155057823,5-Diiodotoluene

Product 1

HCID 691197121-(Cyclopentylthio)-3-iodo-5-methylbenzene

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 1,3-diiodo-5-methylbenzene (2.00 g), tris(dibenzylideneacetone)dipalladium (0) (20 mg), bis(diphenylphosphino)ferrocene (22 mg), triethylamine (1.5 ml) and 1-methyl-2-pyrrolidinone (3 ml) were stirred at to 20° under nitrogen for 1 h. Cyclopentanethiol (0.15 ml) was added and the mixture was heated to 60° for 18 h. The mixtue was cooled to 20° and was treated with phosphate buffer solution (pH 6.5) and water. The mixture was extracted with EtOAc and the extract dried (Na2SO4). Solvent evaporation in vacuo gave a residue which was purified by Flashmaster™ chromatography (silica, 70 g). Elution with cyclohexane gave the title compound (444 mg). LCMS RT=4.21 min.

Workup

  1. temperaturethe mixture was heated to 60° for 18 h
  2. temperatureThe mixtue was cooled to 20°
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe extract dried (Na2SO4)
  5. customSolvent evaporation in vacuo
  6. customgave a residue which
  7. customwas purified by Flashmaster™ chromatography (silica, 70 g)
  8. washElution with cyclohexane

Sources & evidence

ORD record
ord-cb754952dc3642809a6681a11e38cfd1
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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