Hexafluorothioacetone → 4,5-Bis(4-fluorophenyl)-alpha,alpha-bis(trifluoromethyl)-1H-pyrrole-2-methanethiol

HRID 2286535Notes

Reaction equation

HRID 2286535 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[F:20][C:21]([F:29])([F:28])[C:22]([C:24]([F:27])([F:26])[F:25])=[S:23]>C1(C)C=CC=CC=1>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[CH:11]=[C:10]([C:22]([C:24]([F:27])([F:26])[F:25])([C:21]([F:29])([F:28])[F:20])[SH:23])[NH:9][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 574767HexafluorothioacetoneHCID 111079192,3-bis(4-fluorophenyl)-1H-pyrrole

Product 1

HCID 128733584,5-Bis(4-fluorophenyl)-alpha,alpha-bis(trifluoromethyl)-1H-pyrrole-2-methanethiolYield 22.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a solution of 2.6 g (0.01 mole) of 2,3-bis(4-fluorophenyl)-1H-pyrrole in 100 ml toluene was distilled 2.0 g (0.011 mole) of hexafluorothioacetone, prepared by pyrolysis of the dimer according to the method of W. J. Middleton et al., J. Org. Chem., 30, 1375 (1965). The mixture was stirred at room temperature approximately one-half hour, then was concentrated by rotary evaporation. The residue was purified by chromatography on silica gel, eluting with hexane/toluene (80/20). The chromatographed product was recrystallized from hexane to give 1.0 g of product, m.p. 114°-115°.

Workup

  1. customprepared by pyrolysis of the dimer
  2. concentrationwas concentrated by rotary evaporation
  3. customThe residue was purified by chromatography on silica gel
  4. washeluting with hexane/toluene (80/20)
  5. customThe chromatographed product was recrystallized from hexane

Sources & evidence

ORD record
ord-9ad512274fc94b5e9c5410f0a5f10ae8
Source dataset
uspto-grants-1981_05
Patent number
US04267190

Reaction notes

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