Methanol → 3-Bromo-5-methoxypyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](Br)[CH:7]=1.[CH3:9][O-:10].[Na+].CO>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:10][CH3:9])[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A solution of 3,5-dibromopyridine (134a, 20 g, 84.4 mmol) in DMF (200 mL) was stirred at RT under nitrogen atmosphere and then 21.3 mL of sodium methoxide (25% by wt. in methanol (92.8 mmol) was added slowly. The reaction mixture was stirred overnight at 70° C. under N2. The reaction was cooled to RT and quenched with water (200 mL) and extracted with Et2O (2×200 mL). The combined organic extracts was washed with brine, dried (MgSO4) and concentrated in vacuo. The crude 3-bromo-5-methoxypyridine (134b 14.8 g, 93% theory) afforded a colorless oil after purification by flash chromatography on silica gel (EtOAc:hexane 1:10).
Workup
- temperatureThe reaction was cooled to RT
- customquenched with water (200 mL)
- extractionextracted with Et2O (2×200 mL)
- washThe combined organic extracts was washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-152fe4edc59341489631dd7f6fa4cb82
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07189718B2
Reaction notes
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