(5-Chloro-6-(difluoromethoxy)pyridin-3-yl)methanol → 3-Pyridinecarboxaldehyde, 5-chloro-6-(difluoromethoxy)-
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[N:6][C:7]=1[O:8][CH:9]([F:11])[F:10]>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[C:7]([O:8][CH:9]([F:11])[F:10])=[N:6][CH:5]=[C:4]([CH:3]=1)[CH:12]=[O:13]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of (5-chloro-6-(difluoromethoxy)pyridin-3-yl)methanol (1.000 g; 4.77 mmol) in anh. DCM (40 ml) was treated with MnO2 (6.222 g; 71.57 mmol), and the resulting mixture was stirred at rt, under nitrogen, for 3 h. The resulting reaction mixture was then filtered over celite, and the separated solids were washed with DCM. The filtrate was concentrated to dryness under reduced pressure giving 5-chloro-6-(difluoromethoxy)nicotinaldehyde as a yellow oil. LC-MS (conditions A): tR=0.72 min.; no ionisation.
Workup
- customThe resulting reaction mixture
- filtrationwas then filtered over celite
- washthe separated solids were washed with DCM
- concentrationThe filtrate was concentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-736790edd7574fd6b78bae7863fd29ac
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242970B2
Reaction notes
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