Tert-Butylbenzene → HCID 22625489, compound

HRID 277689

Reaction equation

HRID 277689 reaction equation
[I:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=O.[F:9][C:10]([F:21])([F:20])[CH:11]([F:19])[C:12]([F:18])([F:17])[S:13]([OH:16])(=[O:15])=[O:14].[C:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]>ClCCl>[F:21][C:10]([F:9])([F:20])[CH:11]([F:19])[C:12]([F:17])([F:18])[S:13]([O-:16])(=[O:14])=[O:15].[C:22]([C:26]1[CH:31]=[CH:30][C:29]([I+:1][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 7366Tert-ButylbenzeneHCID 92125IodosylbenzeneHCID 97946281-Propanesulfonic acid, 1,1,2,3,3,3-hexafluoro-

Product 1

HCID 22625489HCID 22625489, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4.4 g (20 mmol) of iodosylbenzene was suspended in 100 ml of dry dichloromethane. The suspension was cooled to 0° C. with stirring. 4.65 g (20 mmol) of 3,3,3,2,1,1-hexafluoropropane sulfonic acid (optionally distilled) was added at the same temperature thereto under exclusion of moisture. The mixture was stirred at room temperature for 3 hours. The temperature of the mixture was returned to 0° C., and 2.68 g (20 mmol) of 4-t-butylbenzene was added thereto at that temperature. The temperature of the mixture was returned to room temperature, followed by stirring for 6 hours. Thereafter, the insolubles were removed by filtration. The solvent was removed from the filtrate. The oily residue was purified by recrystallization (twice) from diethyl ether. The structure was confirmed by 1H-NMR (CDCl3): δ=0.81 (s, 9H), 4.98-5.22 (m[d], 1H), 7.18-7.23 (d, 2H), 7.58-7.65 ppm (m, 7H).

Workup

  1. additionwas added at the same temperature
  2. stirringThe mixture was stirred at room temperature for 3 hours
  3. customwas returned to 0° C.
  4. customwas returned to room temperature
  5. stirringby stirring for 6 hours
  6. customThereafter, the insolubles were removed by filtration
  7. customThe solvent was removed from the filtrate
  8. customThe oily residue was purified by recrystallization (twice) from diethyl ether

Sources & evidence

ORD record
ord-10b1fad91dc64ce68db68fd3e18524a1
Source dataset
uspto-grants-2002_03
Patent number
US06358665B1

Linked notes

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