Trifluoromethanesulfonic anhydride → HCID 22390454, compound

HRID 1018814Notes

Reaction equation

HRID 1018814 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, and the reaction mixture is left at 0° C. for 30 mintues and then 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 the solvents are then 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 varying from 100/0 to 99/1 (v/v). 15 g of the compound are obtained.

Workup

  1. waitthe reaction mixture is left at 0° C. for 30 mintues
  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 then 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

Sources & evidence

ORD record
ord-b786e0e5dba948a1a053870f9bc5452f
Source dataset
uspto-grants-2002_11
Patent number
US06482986B1

Reaction notes

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