Trifluoromethanesulfonic anhydride → 2-Acetyl-4-fluorophenyl trifluoromethanesulfonate

HRID 2224628Notes

Reaction equation

HRID 2224628 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[F:16][C:17]1[CH:18]=[CH:19][C:20](O)=[C:21]([C:23](=[O:25])[CH3:24])[CH:22]=1>N1C=CC=CC=1.C(OCC)C>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][C:20]1[CH:19]=[CH:18][C:17]([F:16])=[CH:22][C:21]=1[C:23](=[O:25])[CH3:24])(=[O:8])=[O:9]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 959922-Acetyl-4-fluorophenol

Product 1

HCID 597176142-Acetyl-4-fluorophenyl trifluoromethanesulfonateYield 101.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

Trifluoromethanesulfonic anhydride (8.6 mL, 51 mmol) was added dropwise at 0° C. to a stirring solution of 5′-fluoro-2′-hydroxy-acetophenone (6.4 g, 41 mmol) in pyridine (62 mL). The reaction was stirred overnight from 0° C. to ambient temperature. The reaction solution was diluted with diethyl ether (500 mL). The organic layer was washed with 1 N aqueous hydrochloric acid (1×300 mL), followed by a saturated, aqueous sodium chloride solution (2×300 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a maroon-colored liquid (11.9 g, 100% ). The product was further purified by Kugel-Rohr distillation to afford a yellow oil that solidified upon standing.

Workup

  1. washThe organic layer was washed with 1 N aqueous hydrochloric acid (1×300 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87976d20776a4b68900d43557a124f07
Source dataset
uspto-grants-2008_05
Patent number
US07378427B2

Reaction notes

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