Thionyl bromide → 4-(Bromomethyl)-2-chloropyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][N:3]=1.S(Br)([Br:12])=O>ClCCl>[Br:12][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-chloropyridine-4-methanol (1.02 g, 7.10 mmol) in 15 mL of dichloromethane was added thionyl bromide (1.77 g, 8.53 mmol) dropwise. After 15 min, the reaction was quenched with saturated aqueous ammonium chloride. The organic solution was washed 2× with water, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 4-(bromomethyl)-2-chloropyridine that gave a mass ion (ES+) of 208.0 for [M+H]+.
Workup
- customthe reaction was quenched with saturated aqueous ammonium chloride
- washThe organic solution was washed 2× with water
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-17d0cd4dc70248268dec5a69fed8b35c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846702B2
Reaction notes
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