Triethylamine → 4-(Difluoroacetyl)-3-fluorophenyl trifluoromethanesulfonate

HRID 216339Notes

Reaction equation

HRID 216339 reaction equation
[F:1][CH:2]([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[F:12])=[O:4].CCN(CC)CC.[O:21](S(C(F)(F)F)(=O)=O)[S:22]([C:25]([F:28])([F:27])[F:26])(=O)=[O:23]>C(Cl)Cl>[F:26][C:25]([F:28])([F:27])[S:22]([O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH:2]([F:1])[F:13])=[C:6]([F:12])[CH:7]=1)(=[O:23])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 866384922,2-Difluoro-1-(2-fluoro-4-hydroxyphenyl)ethan-1-one

Product 1

HCID 875355614-(Difluoroacetyl)-3-fluorophenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2,2-difluoro-1-(2-fluoro-4-hydroxyphenyl)ethanone (39.0 g, 0.2 mol) and Et3N (20.7 g, 0.2 mol) in CH2Cl2 at 0° C. was added Tf2O (58 g, 0.2 mol) dropwise while keeping the temperature at 0° C. The ice-salt bath was removed, and when the temperature rose to 25° C., a solution of saturated NaHCO3 was added. The aqueous phase was extracted with CH2Cl2 and the combined extracts were dried over MgSO4, and concentrated, and the residue was purified by column chromatography (PE/EA 10:1) to afford 4-(difluoroacetyl)-3-fluorophenyl trifluoromethanesulfonate as an brown oil.

Workup

  1. customat 0° C
  2. customThe ice-salt bath was removed
  3. customrose to 25° C.
  4. additiona solution of saturated NaHCO3 was added
  5. extractionThe aqueous phase was extracted with CH2Cl2
  6. dry with materialthe combined extracts were dried over MgSO4
  7. concentrationconcentrated
  8. customthe residue was purified by column chromatography (PE/EA 10:1)

Sources & evidence

ORD record
ord-a2147d2d735341b29b214571b9408de3
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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