Carbon Dioxide → 2,6-Difluoro-4-methoxybenzoic acid

HRID 466488Notes

Reaction equation

HRID 466488 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:8]=[C:9]([O:14][CH3:15])[CH:10]=[C:11]([F:13])[CH:12]=1.[C:16](=[O:18])=[O:17].CCOCC>C1COCC1>[F:6][C:7]1[CH:8]=[C:9]([O:14][CH3:15])[CH:10]=[C:11]([F:13])[C:12]=1[C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 27245183,5-DifluoroanisoleHCID 178418339Butyllithium

Product 1

HCID 27782282,6-Difluoro-4-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyllithium (10.0M in hexane; 25.0 ml, 0.25 mol) was added dropwise to a stirred, cooled (-78° C.) solution of 3,5-difluoroanisole (35.9 g, 0.25 mol) in dry THF (200 ml) under dry nitrogen. The stirred mixture was maintained under these conditions for 2.5 h and then poured into a slurry of solid carbon dioxide and dry ether. The product was extracted into 10% sodium hydroxide (twice), the combined basic extracts were acidified with 36% hydrochloric acid, and the product was extracted into ether (twice), the combined ethereal extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo to give a colourless solid.

Workup

  1. temperatureThe stirred mixture was maintained under these conditions for 2.5 h
  2. extractionThe product was extracted into 10% sodium hydroxide (twice), the combined basic extracts
  3. extractionthe product was extracted into ether (twice), the combined ethereal extracts
  4. washwere washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customto give a colourless solid

Sources & evidence

ORD record
ord-8109066076fe4457a75feb71cd1fe34d
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

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