2,2-Difluoro-2-(fluorosulfonyl)acetic acid → HCID 118168965, compound

HRID 588121Notes

Reaction equation

HRID 588121 reaction equation
[OH:1][CH2:2][C@@H:3]([N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:21][C:22]([F:30])(S(F)(=O)=O)C(O)=O>C(#N)C.[Cu]I>[F:21][CH:22]([F:30])[O:1][CH2:2][C@@H:3]([N:10]1[C:11](=[O:20])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]1=[O:19])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 27375162,2-Difluoro-2-(fluorosulfonyl)acetic acidHCID 11032835HCID 11032835, compound

Product 1

HCID 118168965HCID 118168965, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

(S)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione (1.06 g, 3.97 mmol) was dissolved in anhydrous acetonitrile (20 ml), charged with copper (I) iodide (1.133 g, 5.95 mmol), 2,2-difluoro-2-(fluorosulfonyl)acetic acid (0.615 ml, 5.95 mmol), degassed under nitrogen and heated to 80° C. The solution was allowed to stir at 80° C. for 1 hr. The reaction was cooled in an ice bath, quenched with 5 mL water, filtered through a 10 g celite cartridge, and the solvents were removed in vacuo. The residue was purified by MPLC 10-50% EtOAc/hexanes to provide (S)-2-(2-(difluoromethoxy)-1-phenylethyl)isoindoline-1,3-dione. MS: [M+H]+ m/z 318.

Workup

  1. customdegassed under nitrogen
  2. temperatureThe reaction was cooled in an ice bath
  3. customquenched with 5 mL water
  4. filtrationfiltered through a 10 g celite cartridge
  5. customthe solvents were removed in vacuo
  6. customThe residue was purified by MPLC 10-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-be8d548f4dda4c95b2563d6946584079
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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