N-bromobutanimide → 6-(Bromomethyl)-2,3-dichloropyridine
Reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:17][CH2:9][C:4]1[N:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[CH:6][CH:5]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2,3-dichloro-6-methylpyridine (2 g, 12.3 mmol) in carbon tetrachloride (40 mL) was added NBS (2.64 g, 14.8 mmol) followed by AIBN (40 mg, 0.24 mmol). The reaction heated to 80° C. under nitrogen for 3.5 hours. The reaction was cooled and concentrated in vacuo. The residue was sonicated in heptanes and filtered. The filtrate was eluted through a pad of silica using 10% TBME in heptanes to afford the title compound (2.90 g). The crude material was taken on directly to the next step.
Workup
- temperatureThe reaction was cooled
- concentrationconcentrated in vacuo
- customThe residue was sonicated in heptanes
- filtrationfiltered
- washThe filtrate was eluted through a pad of silica using 10% TBME in heptanes
Sources & evidence
- ORD record
- ord-63d69bc5bb9c4944841db91c4f54a566
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328096B2
Reaction notes
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