Methanol → Methyl 2-bromoisonicotinate hydrochloride
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].S(Cl)([Cl:13])=O.[CH3:15]O>>[ClH:13].[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([O:7][CH3:15])=[O:6]Participants
4
Procedure
Into a 500-mL round bottom flask, was placed a solution of 2-bromoisonicotinic acid (10 g, 49.75 mmol, 1.00 equiv) in methanol (200 mL). This was followed by dropwise addition of thionyl chloride (24 g, 203.39 mmol, 4.09 equiv) with stirring at 0° C.-5° C. The resulting solution was stirred for 5 h at 70° C. in an oil bath. The resulting mixture was concentrated under vacuum, to yield 10 g (80%) of methyl 2-bromoisonicotinate hydrochloride as a white solid.
Workup
- customInto a 500-mL round bottom flask, was placed
- stirringThe resulting solution was stirred for 5 h at 70° C. in an oil bath
- concentrationThe resulting mixture was concentrated under vacuum
Sources & evidence
- ORD record
- ord-a78a90593fbc41d7b966fde1b30c02f9
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916569B2
Reaction notes
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