Imidazole → Benzene, (5-iodopentyl)-

HRID 2063936Notes

Reaction equation

HRID 2063936 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:37]I>C(Cl)Cl>[I:37][CH2:11][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 615235-Phenyl-1-pentanol

Product 1

HCID 561241Benzene, (5-iodopentyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-phenyl-pentane-1-ol (1.0 gm, 6.09 mmol) in CH2Cl2 (20 ml), triphenyl phosphine (2.35 gm, 8.52 mmol), imidazole (0.58 gm, 8.52 mmol) and elemental iodine (2.16 gm, 8.52 mmol) was stirred at room temperature for 12 h. The solvent was evaporated under reduced pressure. The residue was diluted with EtOAc (30 ml), H2O (20 ml) was added, separated and the organic phase was washed with brine (30 ml). The organic layer was dried over anhydrous Na2SO4; solvent was evaporated under reduced pressure and the crude product was purified by column chromatography using hexane as eluent. The crude product was purified by column chromatography using hexane as eluent. The pure product was an oily liquid (750 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with EtOAc (30 ml), H2O (20 ml)
  3. additionwas added
  4. customseparated
  5. washthe organic phase was washed with brine (30 ml)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. customsolvent was evaporated under reduced pressure
  8. customthe crude product was purified by column chromatography
  9. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f89fe05568aa4e2892023b560c3357dc
Source dataset
uspto-grants-2012_10
Patent number
US08288410B2

Reaction notes

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