Trifluoroacetic acid → HCID 21553765, compound

HRID 267701Notes

Reaction equation

HRID 267701 reaction equation
C(O)(=O)C.C(O)(=O)C.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([I:16]=O)=[CH:12][CH:11]=1.[S:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26]>C(OC(=O)C)(=O)C>[F:23][C:24]([F:29])([F:28])[C:25]([O-:27])=[O:26].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([I+:16][C:19]2[S:18][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8030ThiopheneHCID 86733151HCID 86733151, compound

Product 1

HCID 21553765HCID 21553765, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Conditions

Temperature
-20 °C

Procedure

4-Chloroiodosobenzene diacetate (17.3 grams; 0.05 mole) was dispersed in a mixture of 15 milliliters each of acetic anhydride and trifluoroacetic acid, and a solution of thiophene (8.4 grams; 0.10 mole) in 60 milliliters of acetic anhydride added slowly thereto. The addition was carried out with stirring in 55 minutes at -20°C. Stirring was continued for 65 minutes at -20°C., and the reaction mixture thereafter warmed and maintained at -3°C. with stirring for 15 hours to insure completion of the reaction. The reaction mixture was concentrated by fractional distillation under reduced pressure up to 50°C., and the resulting residue diluted with 100 milliliters of diethyl ether. During the dilution, the 4-chlorophenyl-2-thienyliodonium trifluoroacetate precipitated as a crystalline solid and was separated by filtration. The solid, recrystallized from a mixture of acetone and normal pentane, melted at 156°-157.5°C.

Workup

  1. additionThe addition
  2. stirringStirring
  3. waitwas continued for 65 minutes at -20°C.
  4. temperaturethe reaction mixture thereafter warmed
  5. temperaturemaintained at -3°C.
  6. stirringwith stirring for 15 hours
  7. customcompletion of the reaction
  8. concentrationThe reaction mixture was concentrated by fractional distillation under reduced pressure up to 50°C.
  9. additionthe resulting residue diluted with 100 milliliters of diethyl ether
  10. customDuring the dilution, the 4-chlorophenyl-2-thienyliodonium trifluoroacetate precipitated as a crystalline solid
  11. customwas separated by filtration
  12. customThe solid, recrystallized from a mixture of acetone and normal pentane, melted at 156°-157.5°C.

Sources & evidence

ORD record
ord-440f524b951d494d9289c4e2df3d0345
Source dataset
uspto-grants-1976_03
Patent number
US03944498

Reaction notes

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