Hydrochloric Acid → 4-Fluorosalicylic acid

HRID 644166Notes

Reaction equation

HRID 644166 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.[C]=O.Cl>O>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:1]([OH:2])=[O:4])=[C:10]([OH:14])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 178418416HCID 178418416, compound

Product 1

HCID 676614-Fluorosalicylic acidYield 52.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

Potassium carbonate (51.6 g, 373 mmol) was dried by heating at 200° C. for 12 hours. This was treated with 3-fluorophenol (16.5 g, 147 mmol) in a sealed container which was then pressurized with carbon monoxide at 61.2 bar. The reaction was heated to 175° C. for 5 hours. Subsequently, the reaction mixture was dissolved in water, acidified with concentrated hydrochloric acid, and filtered. The solid was washed with water, then hexanes. The solid was then dissolved in EtOAc, dried over magnesium sulfate, and concentrated to give 12 g of solid. This crude solid was purified by flash chromatrography using CHCl3/MeOH/HOAc 98:1:1 to give 11 g of a white solid which was recrystallized from toluene to give 9.5 g of the product as needles.

Workup

  1. temperatureThe reaction was heated to 175° C. for 5 hours
  2. filtrationfiltered
  3. washThe solid was washed with water
  4. dissolutionThe solid was then dissolved in EtOAc
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2fd2d8fdf1b6477da09fac94b8f4a845
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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