Trifluoroacetic acid → HCID 20314460, compound

HRID 2419912Notes

Reaction equation

HRID 2419912 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([I:19](OC(=O)C)OC(=O)C)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>C(OC(=O)C)(=O)C>[F:28][C:29]([F:34])([F:33])[C:30]([O-:32])=[O:31].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([I+:19][C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[CH:15][CH:14]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8030ThiopheneHCID 20314474HCID 20314474, compound

Product 1

HCID 20314460HCID 20314460, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent2×

Conditions

Temperature
-10 °C

Procedure

A mixture of thiophene (8.7 g.) and acetic anhydride (60 ml.) is added to a stirred suspension of 4-(4-chlorophenyl)(diacetoxyiodo)benzene (21.7 g.) in a mixture of acetic anhydride (50 ml.) and trifluoroacetic acid (15 ml.) below -10° C. during 1 hour. The mixture is stirred at -10° C. for 2 hours, at ambient temperature for 18 hours and is then filtered. The filtrate is concentrated to small volume in vacuo, and ether is added. The solid so formed is filtered off and crystallised from toluene to give 4-(4-chlorophenyl)phenyl-2-thienyliodonium trifluoroacetate (13.7 g.), m.p. 175°-177° C.

Workup

  1. filtrationis then filtered
  2. concentrationThe filtrate is concentrated to small volume in vacuo, and ether
  3. additionis added
  4. customThe solid so formed
  5. filtrationis filtered off
  6. customcrystallised from toluene

Sources & evidence

ORD record
ord-6f6cb4b5d0f84c888a014b2779c22c72
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

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