Carbon tetrabromide → 2-(Bromomethyl)-6-methylpyridine
Reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>ClCCl>[Br:30][CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To an ice cooled a solution of (6-methylpyridin-2-yl)methanol (400 mg, 3.25 mmol) in dichloromethane (16 mL) under an atmosphere of dry nitrogen was added triphenylphosphine (1278 mg, 4.87 mmol) and carbon tetrabromide (1616 mg, 4.87 mmol). The mixture was stirred for 1 hour. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica, eluting with 2-4% methanol in dichloromethane to give 2-(bromomethyl)-6-methylpyridine as an oil (402 mg).
Workup
- customThe solvent was removed under reduced pressure
- customthe residue was purified by chromatography on silica
- washeluting with 2-4% methanol in dichloromethane
Sources & evidence
- ORD record
- ord-d5b7f4e6014b4c3e92fe9055a43e9c05
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841455B2
Reaction notes
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