Chloroiodomethane → 2-(Chloromethyl)-2-(2,4-difluorophenyl)oxirane

HRID 1935379Notes

Reaction equation

HRID 1935379 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=[O:4].Cl[CH2:14]I.[NH4+].[Cl-].[OH-].[Na+]>C(OCC)C.O1CCCC1>[Cl:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=2[F:12])[CH2:14][O:4]1

Participants

7

Reactant 4

HCID 11644ChloroiodomethaneHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 5880832-Chloro-1-(2,4-difluorophenyl)ethanone

Product 1

HCID 111833262-(Chloromethyl)-2-(2,4-difluorophenyl)oxiraneYield 34.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (−78° C.) mixture of 2-chloro-1(2,4-difluorophenyl)-1-ethanone (30 g), chloroiodomethane (56.4 g) and tetrahydrofuran 267 ml) was added dropwise a 6% solution of methyllithium-lithiumbromide complex in diethylether (215 ml). The reaction mixture was slowly warmed to room temperature and was then hydrolysed with NH4Cl. Aqueous NaOH was added and the mixture was stirred for 1 hour. The organic layer was separated, washed, dried, filtered and the solvent evaporated. The residue was purified over silica gel (eluent: hexane/CH3COOC2H5 98/2). The solvent of the desired fraction was evaporated, yielding 11 g (16.8%) of 2-(chloromethyl)-2-(2,4-difluorophenyl)oxirane (interm. 1).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred for 1 hour
  3. customThe organic layer was separated
  4. washwashed
  5. customdried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified over silica gel (eluent: hexane/CH3COOC2H5 98/2)
  9. customThe solvent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-a9b640d5fe6846aebd25a1833a47064d
Source dataset
uspto-grants-2002_05
Patent number
US06387906B1

Reaction notes

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