Imidazole → 1-(2-iodoethyl)-4-phenyl-1H-imidazole

HRID 2405950Notes

Reaction equation

HRID 2405950 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][N:10]([CH2:12][CH2:13]O)[CH:11]=2)[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:39]I>C(Cl)Cl>[I:39][CH2:13][CH2:12][N:10]1[CH:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[CH:9]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 106314624-Phenyl-1H-imidazole-1-ethanol

Product 1

HCID 867102511-(2-iodoethyl)-4-phenyl-1H-imidazoleYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-phenyl-1H-imidazol-1-yl)ethanol (500 mg, 2.66 mmol, 1 eq) in DCM (10 mL) was added PPh3 (778 mg, 2.96 mmol, 1.1 eq), imidazole (203 mg, 2.98 mmol, 1.1 eq) and iodine (753 mg, 2.97 mmol, 1.1 eq). The reaction mixture was allowed to stir at RT overnight. The organic layer was extracted with 1N HCl. The combined acid extracts were then adjusted to pH˜8 with solid sodium carbonate. The aqueous layer was extracted 2× with Et2O. The combined ether extracts were dried over sodium sulfate, filtered and concentrated to dryness to give 1-(2-iodoethyl)-4-phenyl-1H-imidazole (623 mg, 78% yield) which was used without further purification. LC-MS M+H+298.9.

Workup

  1. extractionThe organic layer was extracted with 1N HCl
  2. extractionThe aqueous layer was extracted 2× with Et2O
  3. dry with materialThe combined ether extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-13e8b87d2d66485b9d900528420d7edb
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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