Methanol → 2'-Fluoro-5'-(methyloxy)-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acid

HRID 1662383Notes

Reaction equation

HRID 1662383 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([C:20]([O:22][CH3:23])=[O:21])=[CH:12][C:13]([C:16]([O:18]C)=[O:17])=[CH:14][CH:15]=1.C1COCC1.CO.[OH-].[K+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][C:11]=1[C:20]([O:22][CH3:23])=[O:21]

Participants

5

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 57706522Dimethyl 2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2,4-dicarboxylate

Product 1

HCID 577057642'-Fluoro-5'-(methyloxy)-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acidYield 100%

Procedure

To a stirred solution of 66.13C (36.50 g, 115 mmol) in THF (70.0 mL, 854 mmol) and MeOH (70.0 mL, 1730 mmol) at 0° C. was added potassium hydroxide (63 mL, 126 mmol) slowly to maintain the temperature below 6° C. The reaction mixture was allowed to warm to room temperature and stirring was continued for 15 hours. The reaction mixture was concentrated in vacuo. 1N HCl was added to the aqueous phase and the resulting mixture was extracted with EtOAc. The organic layer was dried over MgSO4, and concentrated in vacuo to give 2′-fluoro-5′-(methyloxy)-2-((methyloxy)carbonyl)-1,1′-biphenyl-4-carboxylic acid 66.13D as a white solid (35.00 g, 100% yield). MS ESI (pos.) m/e: 322.1 (M+H2O)+, 305.0 (M+H)+.

Workup

  1. temperatureto maintain the temperature below 6° C
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. addition1N HCl was added to the aqueous phase
  4. extractionthe resulting mixture was extracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c00d18a2ea5407297c214875af30d54
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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