Triethylamine → Dimethyl 5-[[(Trifluoromethyl)sulfonyl]oxy]isophthalate

HRID 1096936Notes

Reaction equation

HRID 1096936 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[CH:18]=[C:19]([C:27]([O:29][CH3:30])=[O:28])[CH:20]=[C:21]([CH:26]=1)[C:22]([O:24][CH3:25])=[O:23].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[CH:26]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[CH:20]=[C:19]([CH:18]=1)[C:27]([O:29][CH3:30])=[O:28])(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 10617248Dimethyl 5-[[(Trifluoromethyl)sulfonyl]oxy]isophthalate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

With cooling with ice, trifluoromethanesulfonic acid anhydride (4.04 mL, 24.0 mmol) was added to a mixture of dimethyl 5-hydroxyisophthalate (4.20 g, 20.0 mmol), triethylamine (6.69 mL, 48.0 mmol) and chloroform (40 mL), and stirred for 1 hour with cooling with ice. The reaction mixture was diluted with chloroform, shaken with aqueous saturated sodium hydrogencarbonate solution, then the organic layer was dried with sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography to obtain the title compound as a colorless solid.

Workup

  1. temperaturewith cooling with ice
  2. dry with materialthe organic layer was dried with sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-b6b28b53347b4192b3ca7ee000704093
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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