2,6-Lutidine → Triphenylenyl trifluoromethanesulfonate

HRID 467418Notes

Reaction equation

HRID 467418 reaction equation
O[C:2]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[CH:3]=1.CC1C=CC=C(C)N=1.[F:28][C:29]([F:42])([F:41])[S:30]([O:33]S(C(F)(F)F)(=O)=O)(=[O:32])=[O:31]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:28][C:29]([F:42])([F:41])[S:30]([O:33][C:3]1[C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]=2[CH:18]=[CH:19][CH:2]=1)(=[O:32])=[O:31]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 3016112Triphenylen-2-ol

Product 1

HCID 86647724Triphenylenyl trifluoromethanesulfonateYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Under an argon atmosphere, 12.5 g of 2-hydroxytriphenylene and 0.93 g of 4-dimethylaminopiridine were placed in a flask, 200 mL of methylene chloride was added thereto and the reaction solution was cooled to −78° C. 8.22 g of 2,6-dimethylpiridine was added to the reaction solution and then, 17.3 g of trifluoromethanesulfonic acid anhydride was dropwise added thereto. The reaction solution was stirred for 5 hours while increasing temperature of the reaction solution to room temperature. The deposited solid was collected by filtration, washed with water and methanol and then dried to obtain 17.3 g (yield: 90%) of triphenylenyl trifluoromethanesulfonate.

Workup

  1. temperaturewhile increasing temperature of the reaction solution to room temperature
  2. filtrationThe deposited solid was collected by filtration
  3. washwashed with water and methanol
  4. customdried

Sources & evidence

ORD record
ord-f83cdeeb17f941808b7427d4f2f47738
Source dataset
uspto-grants-2014_01
Patent number
US08623520B2

Reaction notes

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