Sodium Acetate → HCID 66665803, compound

HRID 221746Notes

Reaction equation

HRID 221746 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C:8]2([CH:17]([F:19])[F:18])[NH:13][C:12](=[O:14])[C:11]([CH3:16])([CH3:15])[O:10][CH2:9]2)[CH:7]=1.C([O-])(=O)C.[Na+].[H][H]>CO.C1COCC1.[Pd]>[F:19][CH:17]([F:18])[C:8]1([C:6]2[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=2[F:20])[NH:13][C:12](=[O:14])[C:11]([CH3:16])([CH3:15])[O:10][CH2:9]1

Participants

7

Reactant 3

HCID 517045Sodium AcetateHCID 66665769HCID 66665769, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66665803HCID 66665803, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(5-Bromo-2-fluoro-phenyl)-5-difluoromethyl-2,2-dimethyl-morpholin-3-one (3.14 g, 8.92 mmol) and sodium acetate (1.46 g, 17.83 mmol) were suspended in 100 mL methanol and 10 mL THF. Eventually, 10% Pd on charcoal (315 mg) was added and the reaction mixture was treated with hydrogen (balloon) at rt. After 60 minutes the reaction mixture was filtered over celite and evaporated. The residue was partitioned between aqueous Na2CO3 solution and EtOAc. The layers were separated, washed with brine and EtOAc. The combined organic layers were dried over MgSO4.H2O and evaporated to give 2.42 g of the title compound as a white solid.

Workup

  1. filtrationAfter 60 minutes the reaction mixture was filtered over celite
  2. customevaporated
  3. customThe residue was partitioned between aqueous Na2CO3 solution and EtOAc
  4. customThe layers were separated
  5. washwashed with brine and EtOAc
  6. dry with materialThe combined organic layers were dried over MgSO4.H2O
  7. customevaporated

Sources & evidence

ORD record
ord-33cfecf6f72d465e86b645e7197ba6ae
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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