Carbon Dioxide → 6-Chloro-2-fluoro-3-methoxybenzoic acid

HRID 1879119Notes

Reaction equation

HRID 1879119 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([F:15])[CH:8]=1.[C:16](=[O:18])=[O:17]>O1CCCC1>[Cl:6][C:7]1[C:8]([C:16]([OH:18])=[O:17])=[C:9]([F:15])[C:10]([O:13][CH3:14])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 2231014-Chloro-2-fluoroanisoleHCID 178418339Butyllithium

Product 1

HCID 38560396-Chloro-2-fluoro-3-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (11.7 ml, 18.77 mmol) was added dropwise to a solution of 4-chloro-2-fluoroanisole (2.01 g, 12.52 mmol) in tetrahydrofuran (20 ml) at −78° C. and the reaction was stirred for 30 mins. Crushed solid carbon dioxide was added in one portion and the reaction was then allowed to warm to room temperature. The solvent was evaporated and the residue dissolved in water. Sodium hydroxide (2M to pH˜14) was added and the aqueous layer extracted with ethyl acetate. The aqueous layer was acidified with hydrochloric acid (5M, pH˜1) and the title compound was collected as a colourless solid (2.25 g, 88%). The compound was dried in vacuo.

Workup

  1. additionwas added in one portion
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in water
  4. additionSodium hydroxide (2M to pH˜14) was added
  5. extractionthe aqueous layer extracted with ethyl acetate
  6. customthe title compound was collected as a colourless solid (2.25 g, 88%)
  7. customThe compound was dried in vacuo

Sources & evidence

ORD record
ord-6dc2a7b4c49849f5a87f85b62687aeac
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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