(Diethylamino)sulfur trifluoride → Methyl (3,5-difluorophenyl)fluoroacetate

HRID 133201Notes

Reaction equation

HRID 133201 reaction equation
C(N(S(F)(F)[F:7])CC)C.[F:10][C:11]1[CH:12]=[C:13]([CH:20]=[C:21]([F:23])[CH:22]=1)[CH:14](O)[C:15]([O:17][CH3:18])=[O:16]>C(Cl)Cl>[F:7][CH:14]([C:13]1[CH:12]=[C:11]([F:10])[CH:22]=[C:21]([F:23])[CH:20]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 22312159Methyl 2-(3,5-difluorophenyl)-2-hydroxyacetate

Product 1

HCID 22312713Methyl (3,5-difluorophenyl)fluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of diethylaminosulfur trifluoride (DAST) (1.1 eq) in methylene chloride was cooled to 0° C. and a pre-cooled solution of methyl 3,5-difluoromandelate (1 eq) in methylene chloride was added. The transfer flask was rinsed with a small portion of methylene chloride. After 15 minutes, the cooling bath was removed and the reaction mixture was stirred an additional 40 minutes at ambient temperature. The mixture was poured over ice and the layers separated. The organic phase was washed with saturated NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified via HPLC eluting with 7% ethyl acetate/hexanes providing the title intermediate as a yellow oil.

Workup

  1. washThe transfer flask was rinsed with a small portion of methylene chloride
  2. customthe cooling bath was removed
  3. additionThe mixture was poured over ice
  4. customthe layers separated
  5. washThe organic phase was washed with saturated NaHCO3 and brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified via HPLC
  10. washeluting with 7% ethyl acetate/hexanes providing the title intermediate as a yellow oil

Sources & evidence

ORD record
ord-c02f07b5da3742758feeeae61b1385e0
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

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