Hydroxide → 2-Bromo-3-methoxypyridine
Reaction equation
[OH-].[Br:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][N:4]=1.[CH3:10]I>CS(C)=O>[Br:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][N:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
5.93 g (90.0 mmol) of 85% powdered potassum [sic] hydroxide are suspended in 30 ml of DMSO and heated to 50° C. under argon as the inert gas. 2.54 g (14.6 mmol) of 2-bromo-3-hydroxypyridine dissolved in 10 ml of DMSO are added dropwise to this suspension. This solution is stirred for another 10 minutes, after which 12.3 g (5.30 ml, 33.1 mmol) of methyl iodide are added dropwise over a period of 2 minutes. The addition takes place at such a rate that the reaction temperature is always between 50°-55° C. The reaction [sic] is then stirred at this temperature for another 10 minutes. The finished reaction solution is finally poured onto 100 ml of ground ice. The crude product obtained is recrystallized from ether/petroleum ether (4:1).
Workup
- additionare added dropwise to this suspension
- additionThe addition
- customis always between 50°-55° C
- customThe reaction [sic]
- stirringis then stirred at this temperature for another 10 minutes
- customThe finished reaction solution
- additionis finally poured onto 100 ml of ground ice
Sources & evidence
- ORD record
- ord-b80fb35b3a4e49b6a594f6f936966f90
- Source dataset
- uspto-grants-1993_11
- Patent number
- US05266700
Reaction notes
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