Sodium Acetate → 5-Difluoromethyl-5-(2-fluoro-phenyl)morpholin-3-one

HRID 2196337Notes

Reaction equation

HRID 2196337 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:18])=[C:6]([C:8]2([CH:15]([F:17])[F:16])[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:7]=1.C([O-])(=O)C.[Na+].[H][H]>CO.[Pd]>[F:17][CH:15]([F:16])[C:8]1([C:6]2[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=2[F:18])[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 666657213-Morpholinone,5-(5-bromo-2-fluorophenyl)-5-(difluoromethyl)-HCID 178418361HCID 178418361, compound

Product 1

HCID 666653645-Difluoromethyl-5-(2-fluoro-phenyl)morpholin-3-oneYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(5-Bromo-2-fluoro-phenyl)-5-difluoromethyl-morpholin-3-one (190 g, 586 mmol) [example 42 step e)] and sodium acetate (57.7 g, 703 mmol) were suspended in 1850 mL methanol. 10% Pd on charcoal (18.7 g) was then added and the reaction mixture was shaken in a Parr apparatus in an atmosphere of hydrogen at rt. After 60 minutes the reaction mixture was filtered over celite and evaporated. The residue was dissolved in 2 L TBME and washed with aqueous NaHCO3 and brine. The organic layer was dried over MgSO4.H2O and evaporated to give 143.2 g of the title compound as a white solid.

Workup

  1. filtrationAfter 60 minutes the reaction mixture was filtered over celite
  2. customevaporated
  3. dissolutionThe residue was dissolved in 2 L TBME
  4. washwashed with aqueous NaHCO3 and brine
  5. dry with materialThe organic layer was dried over MgSO4.H2O
  6. customevaporated

Sources & evidence

ORD record
ord-0b7e8ad636b244f788c11c06e8611802
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

Loading…