Trifluoromethanesulfonic anhydride → 4-((Methoxycarbonyl)methyl)-5-chloro-2-methoxyphenyl trifluoromethanesulfonate

HRID 2173338Notes

Reaction equation

HRID 2173338 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13].[O:16](S(C(F)(F)F)(=O)=O)[S:17]([C:20]([F:23])([F:22])[F:21])(=O)=[O:18]>N1C=CC=CC=1>[CH3:15][O:14][C:12](=[O:13])[CH2:11][C:3]1[CH:4]=[C:5]([O:9][CH3:10])[C:6]([O:8][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:18])=[O:16])=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 77230646Methyl (2-chloro-4-hydroxy-5-methoxyphenyl)acetate

Product 1

HCID 1254976274-((Methoxycarbonyl)methyl)-5-chloro-2-methoxyphenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl (2-chloro-4-hydroxy-5-methoxyphenyl)acetate (570 mg, 2.468 mmol) in 10 mL of pyridine was added Tf2O (853 mg, 2.962 mmol) dropwise at 0° C. The resulting mixture was stirred at rt overnight and concentrated to dryness. The residue was dissolved in EtOAc (50 mL), washed with 1 N HCl (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated to give methyl(2-chloro-5-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}phenyeacetate.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in EtOAc (50 mL)
  3. washwashed with 1 N HCl (50 mL), brine (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give methyl(2-chloro-5-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}phenyeacetate

Sources & evidence

ORD record
ord-ec05c533f69642879da80c158c623aff
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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