Trifluoromethanesulfonic anhydride → HCID 22390454, compound

HRID 1071930Notes

Reaction equation

HRID 1071930 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[Cl:16][C:17]1[CH:22]=[C:21]([CH:23]2[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][CH2:24]2)[CH:20]=[CH:19][C:18]=1O>N1C=CC=CC=1.C1(C)C=CC=CC=1>[F:5][C:4]([F:7])([F:6])[S:1]([O:8][C:18]1[CH:19]=[CH:20][C:21]([CH:23]2[CH2:24][CH2:25][C:26]([CH3:29])([CH3:30])[CH2:27][CH2:28]2)=[CH:22][C:17]=1[Cl:16])(=[O:3])=[O:2]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 22390446HCID 22390446, compound

Product 1

HCID 22390454HCID 22390454, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

8.2 ml of triflic anhydride are added at 5° C. to 9.7 g of 2-chloro-4-(4,4-dimethylcyclohexyl)phenol (compound IX.1) in 60 ml of pyridine, the reaction mixture is left to stand for 30 minutes at 0° C., and then the reaction mixture is stirred at room temperature for 12 hours. The reaction mixture is hydrolysed and then extracted with dichloromethane. The organic phase is dried over magnesium sulphate and the solvents are evaporated off under reduced pressure. The residue obtained is taken up in toluene, and then the solvents are evaporated off under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/ethyl acetate mixture which varies from 100/0 to 99/1 (v/v). 15 g of the compound are obtained.

Workup

  1. waitthe reaction mixture is left
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customthe solvents are evaporated off under reduced pressure
  5. customThe residue obtained
  6. customthe solvents are evaporated off under reduced pressure
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica gel
  9. washeluting with a cyclohexane/ethyl acetate mixture which

Sources & evidence

ORD record
ord-c849e5f47c714cc0bc66f7d97c477071
Source dataset
uspto-grants-2005_06
Patent number
US06908914B1

Reaction notes

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