2-Fluorothiophenol → 5-(2-Fluorophenylthio)furan-3-carboxylic Acid

HRID 894246Notes

Reaction equation

HRID 894246 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Br[C:10]1[O:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:10]1[O:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=1

Participants

3

Reactant 2

HCID 5202162-FluorothiophenolHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 211624625-(2-Fluorophenylthio)furan-3-carboxylic Acid

Procedure

Following the procedure of Example 13, o-fluorothiophenol (4.02 g., 31.4 mmoles) was reacted with 5-bromofuran-3-carboxylic acid. Isolation according to the procedure of Example 16 gave crude product as an oil. The product was chromatographed on silica gel with ethyl acetate-1/hexane-5/5% acetic acid as eluant. Combination of clean middle cuts, evaporation to dryness and recrystallization from methanol/water gave purified 5-(2-fluorophenylthio)furan-3-carboxylic acid (266 mg., m.p. 100°-103° C., m/e 238).

Workup

  1. customgave crude product as an oil
  2. customThe product was chromatographed on silica gel with ethyl acetate-1/hexane-5/5% acetic acid as eluant
  3. customCombination of clean middle cuts, evaporation
  4. customto dryness and recrystallization from methanol/water
  5. customgave
  6. custompurified 5-(2-fluorophenylthio)furan-3-carboxylic acid (266 mg., m.p. 100°-103° C., m/e 238)

Sources & evidence

ORD record
ord-61a83ef0a6794ef7b4a4aeba74f8d9f4
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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