Hydrochloric Acid → 2',5'-Difluoro-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acid

HRID 1662546Notes

Reaction equation

HRID 1662546 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[C:10]([C:19]([O:21][CH3:22])=[O:20])=[CH:11][C:12]([C:15]([O:17]C)=[O:16])=[CH:13][CH:14]=1.[OH-].[K+].Cl>C1COCC1.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][C:10]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57707138Dimethyl 2',5'-difluoro-1,1'-biphenyl-2,4-dicarboxylate

Product 1

HCID 577063522',5'-Difluoro-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 83.27A (0.800 g, 2.6 mmol) in THF (7.00 mL) and MeOH (7.00 mL) at 0° C. was slowly added potassium hydroxide (1.4 mL, 2.9 mmol) to maintain the temperature below 6° C. The reaction mixture was then allowed to warm to room temperature and stirred for 19 hours. The reaction was then acidified with 1N HCl and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure to yield 83.27B as a colorless solid (0.76 g, 100% yield).

Workup

  1. customat 0° C.
  2. temperatureto maintain the temperature below 6° C
  3. extractionextracted three times with EtOAc
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. filtrationfiltering
  6. customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e9a4f0a4b1344172958b7c7db58c5b00
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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