4-Methoxybenzyl alcohol → 3-Bromo-5-[(4-methoxyphenyl)methoxy]pyridine
Reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[H-].[Na+].[Br:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18](Br)[CH:19]=1>CS(C)=O>[Br:13][C:14]1[CH:15]=[N:16][CH:17]=[C:18]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:19]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 4-methoxybenzyl alcohol (1.73 g) in DMSO (10 mL) at room temperature was added sodium hydride (500 mg). The reaction mixture was stirred for 75 min and then a solution of 3,5-dibromopyridine (3.0 g) in DMSO (15 mL) was added. The reaction mixture was then heated at 90° C. for 2.5 h and then allowed to cool to room temperature, quenched with water (60 mL) and extracted into diethyl ether (3×60 mL). The combined organics were washed with brine (100 mL), dried (MgSO4), reduced in vacuo and purified by column chromatography to give 3-bromo-5-(4-methoxy-benzyloxy)-pyridine as a white solid (1.76 g).
Workup
- temperatureto cool to room temperature
- customquenched with water (60 mL)
- extractionextracted into diethyl ether (3×60 mL)
- washThe combined organics were washed with brine (100 mL)
- dry with materialdried (MgSO4)
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-9eb5aef999904490aa64d6496a622df8
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802670B2
Reaction notes
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