5-Fluoro-2-methylthiophenol → HCID 21162454, compound

HRID 894250Notes

Reaction equation

HRID 894250 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[SH:9].Br[C:11]1[O:15][CH:14]=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=1>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9][C:11]1[O:15][CH:14]=[C:13]([C:16]([OH:18])=[O:17])[CH:12]=1

Participants

4

Reactant 2

HCID 27590435-Fluoro-2-methylthiophenolHCID 133335605-Bromofuran-3-carboxylic acid

Product 1

HCID 21162454HCID 21162454, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an open flask cuprous oxide (500 mg., 3.5 mmoles) and 2-methyl-5-fluorothiophenol (1.0 g., 7 mmoles) were combined in 35 ml. of dimethylformamide and heated in an oil bath at 135°-140° C. for 2.5 hours. The mixture was cooled slightly, 5-bromofuran-3-carboxylic acid (668 mg., 3.5 mmoles) was added and the mixture refluxed for approximately 16 hours. Crude product was isolated according to Example 16. The resulting oil was crystallized by trituration with water (170 mg.). Recrystallization from methanol/water gave purified 5-(2-methyl-5-fluorophenylthio)furan-3-carboxylic acid (125 mg., m.p. 150°-152° C., m/e 252).

Workup

  1. temperatureThe mixture was cooled slightly
  2. temperaturethe mixture refluxed for approximately 16 hours
  3. customCrude product was isolated
  4. customThe resulting oil was crystallized by trituration with water (170 mg.)
  5. customRecrystallization from methanol/water
  6. customgave
  7. custompurified 5-(2-methyl-5-fluorophenylthio)furan-3-carboxylic acid (125 mg., m.p. 150°-152° C., m/e 252)

Sources & evidence

ORD record
ord-df7ecbdbd59240b8a666daea32310ceb
Source dataset
uspto-grants-1981_08
Patent number
US04282246

Reaction notes

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