Methanol → 3'-Chloro-5-fluoro-6,4'-dimethoxy-biphenyl-3-carboxylic Acid

HRID 1475780Notes

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

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-f63be265893a41b697038d0f462d5cca
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018383B2

Reaction notes

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