Imidazole → 1,1,1,2,2-Pentafluoro-5-iodopentane

HRID 651502Notes

Reaction equation

HRID 651502 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[F:27][C:28]([F:37])([C:33]([F:36])([F:35])[F:34])[CH:29]=[CH:30][CH2:31]O>C(Cl)Cl>[F:27][C:28]([F:37])([C:33]([F:36])([F:35])[F:34])[CH2:29][CH2:30][CH2:31][I:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 544526994,4,5,5,5-Pentafluoropent-2-en-l-ol

Product 1

HCID 120170571,1,1,2,2-Pentafluoro-5-iodopentane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

446 mg of triphenylphosphine is dissolved in 2 cm3 of methylene chloride, cooled down to 10° C., 116 mg of imidazole is added, agitation is carried out for 15 minutes, 431 mg of iodine is added, agitation is carried out for 30 minutes, 0.21 cm3 of 4,4,5,5,5-pentafluoro 2-penten 1-ol is added, agitation is carried out for 4 hours at ambient temperature, the organic phase is washed with a saturated aqueous solution of sodium thiosulphate and a chloromethylenic solution of 4,4,5,5,5-pentafluoro iodopentane is obtained which is used as it is in the continuation of the synthesis. The operation is carried out as indicated in Example 8 Stage F, starting with 618 mg of the thioacetate prepared below in 7 cm3 of methanol and the chloromethylenic solution of the iodated derivative prepared above. 1.2 g of expected product is obtained.

Workup

  1. waitagitation is carried out for 30 minutes
  2. waitagitation is carried out for 4 hours at ambient temperature
  3. washthe organic phase is washed with a saturated aqueous solution of sodium thiosulphate

Sources & evidence

ORD record
ord-27cc0f16930b48fc9666833cc792af8f
Source dataset
uspto-grants-2001_08
Patent number
US06281204B1

Reaction notes

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