Hydrochloric Acid → Ethyl 4-chloro-3,5-difluoropicolinate
Reaction equation
[F:1][C:2]1C(C#N)=[N:4][CH:5]=[C:6]([F:9])[C:7]=1I.[ClH:12].[O:13]1CCO[CH2:15][CH2:14]1.[CH3:19][CH2:20][OH:21]>>[Cl:12][C:7]1[C:6]([F:9])=[CH:5][N:4]=[C:19]([C:20]([O:13][CH2:14][CH3:15])=[O:21])[C:2]=1[F:1]Participants
5
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 3,5-difluoro-4-iodopicolinonitrile (8.0 g, 30.1 mmol) in EtOH (50 mL) was added 4N HCl in 1,4-dioxane (50 mL, 30.1 mmol) and the mixture was heated at 60° C. for 15 hours. The reaction was cooled to room temperature and evaporated under reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed with saturated NaHCO3 solution (100 mL) and brine. The organics were combined and dried over Na2SO4 and evaporated. This material was purified on silica gel chromatography eluted with hexane/EtOAc (0-100%) to give ethyl 4-chloro-3,5-difluoropicolinate. MS [M+H] found 222.1.
Workup
- temperatureThe reaction was cooled to room temperature
- customevaporated under reduced pressure
- dissolutionThe residue was dissolved in EtOAc (100 mL)
- washwashed with saturated NaHCO3 solution (100 mL) and brine
- dry with materialdried over Na2SO4
- customevaporated
- customThis material was purified on silica gel chromatography
- washeluted with hexane/EtOAc (0-100%)
Sources & evidence
- ORD record
- ord-24499dc872f742ab966887d77b55f0eb
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073918B2
Reaction notes
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