Methanol → 3,6-Difluoro-2-methoxypyridine
Reaction equation
F[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[N:3]=1.[CH3:10][OH:11].C[O-].[Na+]>O>[F:8][C:7]1[C:2]([O:11][CH3:10])=[N:3][C:4]([F:9])=[CH:5][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
step 1—To a flask containing 2,3,6-trifluoropyridine (2 g, 15 mmol) was added MeOH (5 mL) followed by methanolic NaOMe (5 mL, 25% NaOMe in MeOH). An exothermic reaction occurred and some solid formed. The reaction was stirred for 10 min and diluted with H2O. The solid was filtered and washed with H2O. The solid was dissolved in EtOAc, washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 1.5 g (69%) of 3,6-difluoro-2-methoxy-pyridine (140). The recovered material was used without further purification.
Workup
- customAn exothermic reaction
- customsome solid formed
- filtrationThe solid was filtered
- washwashed with H2O
- dissolutionThe solid was dissolved in EtOAc
- washwashed sequentially with water and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-0f3f31c895c54efe835966cec79ec1f1
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08487103B2
Reaction notes
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