Iodopentafluoroethane → HCID 23324899, compound

HRID 1380915Notes

Reaction equation

HRID 1380915 reaction equation
[F:1][C:2](I)([F:7])[C:3]([F:6])([F:5])[F:4].C[Mg]Br.C([O:14][C:15]([C:17]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)([OH:24])[CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)=O)C.[Cl-].[NH4+]>CCOCC.O>[OH:24][C:17]([C:25]1[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=1)([C:15](=[O:14])[C:2]([F:7])([F:1])[C:3]([F:6])([F:5])[F:4])[CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1

Participants

7

Reactant 4

HCID 9636IodopentafluoroethaneHCID 25517Ammonium ChlorideHCID 23324896HCID 23324896, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 23324899HCID 23324899, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Gaseous pentafluoroethyl iodide (5 g., 0.02M) was passed into a flask containing dry ether (40 ml.) at -70° and fitted with a dry-ice condenser. A 3 molar solution of methylmagnesium bromide (5.8 ml., 0.017M) was then added over 5 minutes keeping the temperature between -70° and -65°. The mixture was then stirred at -70° for 1/2 hour. 1-Ethoxycarbonyl-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol (1.3 g., 0.0047M) in dry ether (10 ml.) was then added over 10 minutes keeping the temperature at -65° or below. The mixture was then stirred at -70° for 1 hour and was then allowed to warm to -25° over 11/2 hours. A solution of ammonium chloride (5 g.) in water (30 ml.) was then added. The ether layer was separated and the aqueous layer was extracted further with ether (2×40 ml.). The ether layers were combined, dried (MgSO4) and evaporated to give the crude title compound as an oil. The oil was purified by chromatography on silica (230-400 mesh) eluting with ethyl acetate:60°-80° petrol (4:1, by volume) to give the title compound, 1.2 g (55% yield). The compound was recrystallised from cyclohexane, m.p. (after said recrystallisation) 128°-132°.

Workup

  1. customfitted with a dry-ice condenser
  2. customthe temperature between -70° and -65°
  3. customat -65° or below
  4. stirringThe mixture was then stirred at -70° for 1 hour
  5. temperatureto warm to -25° over 11/2 hours
  6. customThe ether layer was separated
  7. extractionthe aqueous layer was extracted further with ether (2×40 ml.)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give the crude title compound as an oil
  11. customThe oil was purified by chromatography on silica (230-400 mesh)
  12. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-0c9ed3f22fce4ac3a62c63c7baaa0e28
Source dataset
uspto-grants-1986_04
Patent number
US04584307

Reaction notes

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