2,3,5,6-Tetrafluorobenzenethiol → HCID 21162428, compound

HRID 894249Notes

Reaction equation

HRID 894249 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[SH:11].Br[C:13]1[O:17][CH:16]=[C:15]([C:18]([OH:20])=[O:19])[CH:14]=1>CN(C)C=O>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[C:3]=1[S:11][C:13]1[O:17][CH:16]=[C:15]([C:18]([OH:20])=[O:19])[CH:14]=1

Participants

4

Reactant 2

HCID 698592,3,5,6-TetrafluorobenzenethiolHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 21162428HCID 21162428, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In an open flask, cuprous oxide (1.95 g., 13.7 mmoles) was combined with 2,3,5,6-tetrafluorothiophenol (5.0 g., 27.4 mmoles) in 40 ml. of dimethylformamide and heated at 140° C. for 2 hours. The reaction was cooled, 5-bromofuran-3-carboxylic acid (2.62 g., 13.7 mmoles) in 50 ml. of dimethylformamide was added, the reaction mixture refluxed for 2 hours, and product (2.75 g.) isolated according to the procedure of Example 9. Recrystallization from methanol/water gave purified 5-(2,3,5,6-tetrafluorophenylthio)furan-3-carboxylic acid (1.78 g., m.p. 150°-153° C., m/e 292).

Workup

  1. temperatureThe reaction was cooled
  2. temperaturethe reaction mixture refluxed for 2 hours
  3. customproduct (2.75 g.) isolated
  4. customRecrystallization from methanol/water
  5. customgave
  6. custompurified 5-(2,3,5,6-tetrafluorophenylthio)furan-3-carboxylic acid (1.78 g., m.p. 150°-153° C., m/e 292)

Sources & evidence

ORD record
ord-fb2cbc8c95e740b3850cd1f8540dff74
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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