Trifluoromethanesulfonic anhydride → Methyl 5-formyl-2-(trifluoromethylsulfonyloxy)benzoate

HRID 1848826Notes

Reaction equation

HRID 1848826 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].[CH:16]([C:18]1[CH:19]=[CH:20][C:21](O)=[C:22]([CH:27]=1)[C:23]([O:25][CH3:26])=[O:24])=[O:17]>C(Cl)Cl>[CH:16]([C:18]1[CH:19]=[CH:20][C:21]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[C:22]([CH:27]=1)[C:23]([O:25][CH3:26])=[O:24])=[O:17]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 14363598Methyl 5-Formylsalicylate

Product 1

HCID 15466849Methyl 5-formyl-2-(trifluoromethylsulfonyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triflic anhydride (7.74 mL) was added to methyl 5-formyl-2-hydroxybenzoate (7.5 g) in 150 mL CH2Cl2 at 0° C., and the reaction mixture was stirred and allowed to warm to room temperature over 3 hours. The reaction mixture was diluted with CH2Cl2 (150 mL), washed 3× with brine, dried over Na2SO4, filtered, and concentrated. The product was used without further purification.

Workup

  1. washwashed 3× with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was used without further purification

Sources & evidence

ORD record
ord-0bbbb7405a0e4db4ac3221c4e9cc534b
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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