2-Iodobenzoic acid → 2-[(4-Fluorophenyl)sulfanyl]benzoic acid

HRID 2049683Notes

Reaction equation

HRID 2049683 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][CH:19]=1>[N+](C1C=CC=CC=1)([O-])=O.[Cu]>[F:17][C:18]1[CH:23]=[CH:22][C:21]([S:24][C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 69412-Iodobenzoic acidHCID 11430Potassium Carbonate3×HCID 677894-Fluorothiophenol

Product 1

HCID 144187682-[(4-Fluorophenyl)sulfanyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7416NitrobenzeneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 147 g of iodobenzoic acid and 45.5 g of potassium carbonate in 57 ml of nitrobenzene is maintained with stirring at 160° C. for 40 minutes. Thereafter, 46.5 of additional potassium carbonate are added, followed by the addition of 73.1 g of 4-fluorothiophenol, another 46.5 g of potassium carbonate and 0.35 g of copper powder. The reaction mixture is stirred in a 160° C. bath for 45 minutes. The resulting solid is collected and then cooled to 0° C. before being mixed with 100 ml of water and 220 ml of 6 N hydrochloric acid. The aqueous mixture is then diluted to 1 liter total volume before being stirred with 450 ml of chloroform. The resulting residue white solid is collected and washed successively with chloroform and water. The solid is dissolved in hot acetone and the acetone solution is successively filtered and cooled to provide a white crystalline product. The product is recrystallized from acetone and then converted to a salt with potassium carbonate. The salt is dissolved in water and the aqueous solution is acidified with 1 N hydrochloric acid to provide 2-(4-fluorophenylthio)benzoic acid.

Workup

  1. temperatureis maintained
  2. stirringThe reaction mixture is stirred in a 160° C. bath for 45 minutes
  3. customThe resulting solid is collected
  4. temperaturecooled to 0° C.
  5. additionbefore being mixed with 100 ml of water and 220 ml of 6 N hydrochloric acid
  6. additionThe aqueous mixture is then diluted to 1 liter total volume
  7. stirringbefore being stirred with 450 ml of chloroform
  8. customThe resulting residue white solid is collected
  9. washwashed successively with chloroform and water
  10. dissolutionThe solid is dissolved in hot acetone
  11. filtrationthe acetone solution is successively filtered
  12. temperaturecooled
  13. customto provide a white crystalline product
  14. customThe product is recrystallized from acetone
  15. dissolutionThe salt is dissolved in water

Sources & evidence

ORD record
ord-157364e351c44b4981fb9fa4ac901c3e
Source dataset
uspto-grants-1980_04
Patent number
US04198420

Reaction notes

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