Methanol → Methyl 5-bromopyridine-2-carboxylate
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:15]O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:15])=[O:9])=[N:6][CH:7]=1Participants
4
Procedure
To a 100 mL round bottle flask with 5-bromopicolinic acid (7.0 g, 35 mmol) in methanol (60 mL) was added dropwise thionyl chloride (3.0 mL) at ambient temperature. After addition the reaction mixture was heated to reflux for 3 h. Methanol was removed and ethyl acetate (80 mL) was added to the residue and was adjusted pH to 7.0 by addition of sodium bicarbonate solution. The organic phase was separated and dried over sodium sulfate. The organic solvent was removed and methyl 5-bromopicolinate 2 was obtained as a white solid which was used for the next step of the reaction without further purification. Yield: 6.57 g, 86.9%.
Workup
- additionAfter addition the reaction mixture
- temperaturewas heated
- temperatureto reflux for 3 h
- customMethanol was removed
- additionethyl acetate (80 mL) was added to the residue
- additionwas adjusted pH to 7.0 by addition of sodium bicarbonate solution
- customThe organic phase was separated
- dry with materialdried over sodium sulfate
- customThe organic solvent was removed
Sources & evidence
- ORD record
- ord-837d313458db48f984180e448977c7bb
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096587B2
Reaction notes
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