Imidazole → (4-Iodobutyl)benzene

HRID 2095420Notes

Reaction equation

HRID 2095420 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:36]I>C1(C)C=CC=CC=1>[I:36][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 76889Benzenebutanol

Product 1

HCID 12709818(4-Iodobutyl)benzeneYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 4-phenyl-1-butanol (601 mg, 4.0 mmol), Ph3P (1.57 g, 6.0 mmol, 1.5 equiv.) and imidazole (409 mg, 6.0 mmol, 1.5 equiv.) in toluene (20 mL) was added I2 (1.52 g, 6.0 mmol, 1.5 equiv.) at 0° C. The mixture was allowed to stand overnight, and the reaction was quenched with saturated Na2S2O3 solution. The mixture was extracted with hexane/EtOAc 10:1, and the organic layer was washed with brine and dried over Na2SO4. After concentration, the residue was filtrated through Celite, and the Celite was washed with hexane. After removal of the solvent, (4-iodobutyl)benzene (1.04 g, 100%) was obtained as a pale yellow oil, which was used in the subsequent step without purification.

Workup

  1. customthe reaction was quenched with saturated Na2S2O3 solution
  2. extractionThe mixture was extracted with hexane/EtOAc 10:1
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. filtrationthe residue was filtrated through Celite
  7. washthe Celite was washed with hexane
  8. customAfter removal of the solvent

Sources & evidence

ORD record
ord-8a04f54e7b9348a3b62a49d25edff401
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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