Hydrochloric Acid → 3-Fluoro-5-methoxybenzoic acid

HRID 2368914Notes

Reaction equation

HRID 2368914 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9](F)[CH:10]=1)[C:5]([OH:7])=[O:6].[CH3:12][O-:13].[Na+].Cl>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:13][CH3:12])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1012653,5-Difluorobenzoic acidHCID 10942334Sodium Methoxide

Product 1

HCID 219424693-Fluoro-5-methoxybenzoic acidYield 74.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3,5-difluoro-benzoic acid (6.38 g, 40.3 mmol) in DMF (10 mL), NaOMe (6.48 g, 121 mmol) was added at room temperature. The mixture was stirred at 120° C. for 12 h, cooled to room temperature and filtered. The solid obtained was dissolved in H2O and pH was adjusted to 3-4 with 4M aqueous HCl solution. The mixture was filtered again and the white solid was washed with water (3×10 mL) to give 5.1 g of 3-fluoro-5-methoxybenzoic acid. 1H NMR (CDCl3): δ 7.37-7.43 (m, 2H), 6.83-6.88 (m, 1H), 3.86 (s, 3H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customThe solid obtained
  4. filtrationThe mixture was filtered again
  5. washthe white solid was washed with water (3×10 mL)

Sources & evidence

ORD record
ord-965f477be8324953804f0e3799b27a8c
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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