Methanol → 3'-Chloro-5-fluoro-6,4'-dimethoxy-biphenyl-3-carboxylic Acid
Reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([Cl:22])[CH:15]=2)[C:8]([O:12][CH3:13])=[C:9]([F:11])[CH:10]=1)=[O:4].CO.[OH-].[Na+].OS([O-])(=O)=O.[Na+]>O>[Cl:22][C:16]1[CH:15]=[C:14]([C:7]2[C:8]([O:12][CH3:13])=[C:9]([F:11])[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
500 mg of 3′-Chloro-5-fluoro-6,4′-dimethoxy-biphenyl-3-carboxylic acid methyl ester were dissolved using 10 ml of methanol and 1.8 ml of a 1M aqueous NaOH-solution added. The reaction mixture was stirred at 60° C. for 5 h and was then allowed to cool to room temperature. The reaction mixture was then poured into 25 ml of water and acidified to pH=4 using aqueous NaHSO4-solution. The mixture was extracted three times using 20 ml of EA each. The organic layer was dried using MgSO4 and evaporated to yield 430 mg of the title compound that was used without further purification.
Workup
- additionadded
- temperatureto cool to room temperature
- extractionThe mixture was extracted three times
- customThe organic layer was dried
- customevaporated
Sources & evidence
- ORD record
- ord-9b89064f988c4cef822c48ac38af5733
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618304B2
Reaction notes
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