Methanol → 4-Amino-6-(4-bromo-2,5-difluorophenyl)-3-chloro-5-fluoropicolinic acid
Reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([Br:16])=[CH:11][C:10]=2[F:17])[N:5]=[C:4]([C:18]([O:20]C)=[O:19])[C:3]=1[Cl:22].CO.[OH-].[Na+]>CC(C)=O>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[C:13]([F:15])[C:12]([Br:16])=[CH:11][C:10]=2[F:17])[N:5]=[C:4]([C:18]([OH:20])=[O:19])[C:3]=1[Cl:22]Participants
5
Conditions
- Temperature
- 20 °C
Procedure
To a solution of methyl 4-amino-6-(4-bromo-2,5-difluorophenyl)-3-chloro-5-fluoropicolinate (0.160 g, 0.404 mmol) in a 1:1 mixture of MeOH (0.674 mL) and acetone (0.674 mL) was added a 2 N aqueous solution of sodium hydroxide (0.607 mL, 1.213 mmol). The reaction mixture was stirred at 20° C. overnight. The reaction mixture was concentrated, poured into a 2 N aqueous solution of HCl, and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, concentrated and dried in vacuo to afford the title compound as a light brown solid (126 mg, 82%).
Workup
- concentrationThe reaction mixture was concentrated
- additionpoured into a 2 N aqueous solution of HCl
- extractionextracted with EtOAc (3×)
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customdried in vacuo
Sources & evidence
- ORD record
- ord-542ab14f28aa40769cb70943d826e0b9
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09113629B2
Reaction notes
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