Imidazole → 2-Iodomethyl-1-(4-methoxybenzyloxy)-4-methylbenzene

HRID 660789Notes

Reaction equation

HRID 660789 reaction equation
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[CH3:27][O:28][C:29]1[CH:45]=[CH:44][C:32]([CH2:33][O:34][C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:36]=2[CH2:42]O)=[CH:31][CH:30]=1>C(Cl)Cl.C1COCC1>[I:25][CH2:42][C:36]1[CH:37]=[C:38]([CH3:41])[CH:39]=[CH:40][C:35]=1[O:34][CH2:33][C:32]1[CH:44]=[CH:45][C:29]([O:28][CH3:27])=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 63325270[2-(4-Methoxybenzyloxy)-5-methylphenyl]-methanol

Product 1

HCID 688425672-Iodomethyl-1-(4-methoxybenzyloxy)-4-methylbenzene

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of imidazole (1.52 g, 22.32 mmol) and triphenylphosphine (5.85 g, 22.32 mmol) in methylene chloride (30 mL)/THF (15 mL) is added iodine (5.67 g, 22.32 mmol) in portions and the mixture is stirred at RT for 3 h. To this is added dropwise a solution of [2-(4-methoxybenzyloxy)-5-methylphenyl]-methanol (4.80 g, 18.6 mmol) in THF (15 mL) and the mixture is stirred at RT for 18 h. The mixture is concentrated and the insoluble material is filtered. The filtrate is evaporated and the residue is purified by column chromatography using a gradient of 0-75% EtOAc/hexane as eluent to give the title compound as a brown oil.

Workup

  1. stirringthe mixture is stirred at RT for 18 h
  2. concentrationThe mixture is concentrated
  3. filtrationthe insoluble material is filtered
  4. customThe filtrate is evaporated
  5. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-d9107bd9143b496085888871b99fb842
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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