Azobisisobutyronitrile → 7-(Bromomethyl)quinoline
Reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:19])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 7-methylquinoline (0.10 g, 0.70 mmol) in 5 ml of CCl4 was added NBS (0.14 g, 0.77 mmol) and AIBN (0.025 g, 0.15 mmol). The reaction mixture was heated at 100° C. for 2 h under nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica (230-400M) using 1% ethyl acetate/hexane eluent to give the desired product (0.090 g, 58%).
Workup
- customAfter the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure
- customthe residue was purified by column chromatography on silica (230-400M)
Sources & evidence
- ORD record
- ord-66ded7ddc0234daaae4ba99bfa3da2c4
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865736B2
Reaction notes
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