HCID 23372826, compound → HCID 23372782, compound

HRID 1899068Notes

Reaction equation

HRID 1899068 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11](C(O)=O)=[CH:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1.C(OCC)(=O)C.[Cu]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][CH:11]=[CH:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 23372826HCID 23372826, compound

Product 1

HCID 23372782HCID 23372782, compoundYield 57.4%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 7047QuinolineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(4-fluorophenyl)-4-(4-nitrophenyl)thiophene-2-carboxylic acid (7.6 g) and copper powder (1.6 g) in quinoline (12 ml) was stirred and refluxed for 7 hours. The reaction mixture was diluted with ethyl acetate and filtered. The filtrate was washed with water, brine, dilute hydrochloric acid and brine, successively, dried and evaporated. The residue (7.3 g) was purified by column chromatography on silica gel (80 g) eluting with a mixture of hexane and toluene (2:1) to give yellow orange crystals of 2-(4-fluorophenyl)-3-(4-nitrophenyl)thiophene (3.8 g).

Workup

  1. temperaturerefluxed for 7 hours
  2. filtrationfiltered
  3. washThe filtrate was washed with water, brine, dilute hydrochloric acid and brine
  4. customsuccessively, dried
  5. customevaporated
  6. customThe residue (7.3 g) was purified by column chromatography on silica gel (80 g)
  7. washeluting with a mixture of hexane and toluene (2:1)

Sources & evidence

ORD record
ord-473e37a6866243f49894298d75f89ff3
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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