Trichloroacetonitrile → 2,4-Difluorobenzyl trichloroacetimidate
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
Conditions
- Temperature
- -15 °C
Procedure
A 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
- custom3 h at ambient temperature the phases were separated
- extractionThe aqueous phase was extracted twice with CH2Cl2
- dry with materialThe combined organic phases were dried with MgSO4
- filtrationThe residue was filtered through celite and
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f9d45d4a92b04cba80d3a3d7ca7aa396
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06291687B1
Reaction notes
Loading…