Azobisisobutyronitrile → 6-Bromomethyl-nicotinic acid methyl ester
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.C1C(=O)N([Br:19])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Br:19][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1Participants
6
Conditions
- Temperature
- 80 °C
Procedure
Methyl 6-methylnicotinate (1.05 g, 10 mmol) was dissolved in ethyl acetate (50 ml), and NBS (3.56 g, 20 mmol) and AIBN (329 mg, 2 mmol) were added thereto. The reaction mixture was stirred at 80° C. for 3 hours, combined with an aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:ethyl acetate/hexane=¼) to give the title compound (682 mg, 28%) as an orange amorphous compound.
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluent:ethyl acetate/hexane=¼)
Sources & evidence
- ORD record
- ord-8ad3cf375be643c2b8d2c5cc1ca6bef4
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07300935B2
Reaction notes
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