Trichloroacetonitrile → 2,4-Difluorobenzyl trichloroacetimidate

HRID 2296818

Reaction equation

HRID 2296818 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[Cl:11][C:12]([Cl:16])([Cl:15])[C:13]#[N:14]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.[OH-].[K+]>[Cl:11][C:12]([Cl:16])([Cl:15])[C:13](=[NH:14])[O:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([F:10])=[CH:9][C:2]=1[F:1]

Participants

6

Reactant 2

HCID 11011TrichloroacetonitrileHCID 918672,4-Difluorobenzyl alcohol

Product 1

HCID 110770742,4-Difluorobenzyl trichloroacetimidateYield 92%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
-15 °C

Procedure

Tetrabutyl ammonium hydrogen sulphate (15 mg) was added to 2,4-difluorobenzylalcohol (1.0 g, 6.94 mmol) in CH2Cl2 (10 ml) and KOH (50%, 10 ml). This mixture was cooled to −15° C. prior to the addition of trichloroacetonitrile (1.2 ml, 8.32 mmol). After 30 min at −15° C. and 3 h at ambient temperature the phases were separated. The aqueous phase was extracted twice with CH2Cl2. The combined organic phases were dried with MgSO4 and reduced to one third. The residue was filtered through celite and concentrated to give the crude 2,4-difluorobenzyl trichloroacetimidate (1.83 g, 92%) as a yellow oil.

Workup

  1. custom3 h at ambient temperature the phases were separated
  2. extractionThe aqueous phase was extracted twice with CH2Cl2
  3. dry with materialThe combined organic phases were dried with MgSO4
  4. filtrationThe residue was filtered through celite and
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-28cd121bda794ab8b9cb5eef5712f152
Source dataset
uspto-grants-2002_12
Patent number
US06489364B2

Linked notes

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