Potassium Hydroxide → 2'-Fluoro-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acid

HRID 1662415Notes

Reaction equation

HRID 1662415 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:18]([O:20][CH3:21])=[O:19])=[CH:10][C:11]([C:14]([O:16]C)=[O:15])=[CH:12][CH:13]=1.[OH-].[K+]>C1COCC1.CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 57706591Dimethyl 2'-fluoro-1,1'-biphenyl-2,4-dicarboxylate

Product 1

HCID 577067632'-Fluoro-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 66.32A (1.00 g, 3.5 mmol) in THF (70.0 mL) and MeOH (70.0 mL) at 0° C. was slowly added potassium hydroxide (1.9 mL, 3.8 mmol) to maintain the temperature below 6° C. The reaction mixture was allowed to warm to room temperature and stirred for 48 hours. The reaction mixture was then concentrated in vacuo, 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 and to give a white solid 66.32B (0.90 g, 95% yield).

Workup

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

Sources & evidence

ORD record
ord-96503ff0837841a9bc59ec8edb4b8a70
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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