Imidazole → Iodomethylcycloheptane

HRID 1018845Notes

Reaction equation

HRID 1018845 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[CH:27]1([CH2:34]O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(Cl)Cl>[CH:27]1([CH2:34][I:25])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 78193Cycloheptanemethanol

Product 1

HCID 2763013IodomethylcycloheptaneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of triphenylphosphine (24.59 g; 92.8 mmol) and imidazole (6.40 g; 93.1 mmol) in methylene chloride (100 mL) cooled to 0° C. and Iodine (23.52 g; 92.7 mmol) was added portionwise over a 10 minute period. A solution of cycloheptane methanol (9.14 g; 71.3 mmol) dissolved in methylene chloride (50 mL) was then added over a 5 minute period. The cooling bath was removed and the mixture allowed to warm to room temperature and stirred overnight. The mixture was diluted with methylene chloride, washed with water and the organic layer dried (magnesium sulfate), filtered and concentrated in vacuo. The crude product was chromatographed (eluent:hexanes) to give 15.35 g (93%) of cycloheptylmethyl iodide as an oil.

Workup

  1. additionwas then added over a 5 minute period
  2. customThe cooling bath was removed
  3. additionThe mixture was diluted with methylene chloride
  4. washwashed with water
  5. dry with materialthe organic layer dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was chromatographed (eluent:hexanes)

Sources & evidence

ORD record
ord-3cac22079622436f890dd99fc7454bfd
Source dataset
uspto-grants-2002_11
Patent number
US06482951B2

Reaction notes

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