Hydrochloric Acid → 4-(4-Bromo-2,3-difluorophenyl)-2-methylnicotinic acid
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16]C)=[O:15])=[C:12]([CH3:18])[N:11]=[CH:10][CH:9]=2)=[C:4]([F:19])[C:3]=1[F:20].[OH-].[Na+].Cl>CO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH3:18])[N:11]=[CH:10][CH:9]=2)=[C:4]([F:19])[C:3]=1[F:20]Participants
Procedure
To a solution of methyl 4-(4-bromo-2,3-difluorophenyl)-2-methylnicotinate (800 mg, 2.34 mmol) in MeOH (10 mL) was added NaOH (935 mg, 23.38 mmol) in Water (10 mL). The reaction mixture was stirred at room temperature for 16 hrs. The reaction mixture was evaporated under reduced pressure and the residue obtained was adjusted to pH ˜3 by adding 1.5N HCl solution. The product was extracted with dichloromethane and the layers were separated. The organic phase was dried over Na2SO4, and concentrated under reduced pressure to afford 4-(4-bromo-2,3-difluorophenyl)-2-methylnicotinic acid (700 mg, 2.133 mmol, 91% crude yield) as an off-white solid which was carried on without further purification. LC/MS (ESI) m/e 330.0 [(M+2H)+, calcd for C13H10BrF2NO2 330.1]; LC/MS retention time (method C): tR=1.34 min.
Workup
- customThe reaction mixture was evaporated under reduced pressure
- customthe residue obtained
- extractionThe product was extracted with dichloromethane
- customthe layers were separated
- dry with materialThe organic phase was dried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-9fc3f6cdbf5d41e09719704f1e552538
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901305B2
Reaction notes
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