Hydrochloric Acid → 3-(3,4-Difluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2(5H)-furanone

HRID 357230Notes

Reaction equation

HRID 357230 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=O.C1CCN2C(=NCCC2)CC1.Cl>C(#N)C.C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:12])[O:11][CH2:14][C:15]=2[C:17]2[CH:18]=[CH:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69571(3,4-Difluorophenyl)acetic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

Product 1

HCID 1279233-(3,4-Difluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2(5H)-furanone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3,4-difluorophenylacetic acid (ALDRICH CHIMICAL) (10 g) and 2-bromo-1-(4-(methylsulfonyl)phenyl)ethanone (Example 9, Step 1) (17.3 g) in acetonitrile (200 mL) at room temperature was added slowly triethylamine (20.2 mL). After 1 h at room temperature, the mixture was cooled in an ice bath and treated with 17.4 mL of DBU. After 2 h at 0° C., the mixture was treated with 200 mL of 1N HCl and the product was extracted with EtOAc, dried over Na2SO4 and concentrated. The residue was applied on top of a silica gel plug (sintered glass funnel) eluted with 75% EtOAc/hexane, giving after evaporation of the solvent and swish in ethyl acetate, 10 g of the title compound.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. waitAfter 2 h at 0° C.
  3. extractionthe product was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. washeluted with 75% EtOAc/hexane
  7. customgiving
  8. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-a0a9ac4109aa479c88e7cead3b32435e
Source dataset
uspto-grants-1998_11
Patent number
US05840746

Reaction notes

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