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

HRID 1182386Notes

Reaction equation

HRID 1182386 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]>ClCCl>[F:10][C:11]1[CH:12]=[C:13]([CH:14]([F:7])[C:15]([O:17][CH3:18])=[O:16])[CH:20]=[C:21]([F:23])[CH:22]=1

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

2.3 g of N-ethyl-N-(trifluoro-λ4-sulfanyl)-1-ethanamine are added dropwise at 20° C. to 2 g of methyl 3,5-difluoromandelate, obtained in step 2.1, in solution in 25 ml of dichloromethane, and the mixture is stirred for 18 hours at room temperature. The reaction medium is taken up in dichloromethane and washed with water, with a saturated aqueous sodium hydrogen carbonate solution, and then with a hydrochloric acid solution (0.5 N). The organic phase is dried over anhydrous sodium sulfate and concentrated to give 1.9 g of oil.

Workup

  1. washwashed with water, with a saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f22e2282d53e4c0ca28af224d2e2820f
Source dataset
uspto-grants-2007_10
Patent number
US07288659B2

Reaction notes

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