Potassium Carbonate → 4-(2-Fluoro-4-nitrophenyl)morpholin-3-one

HRID 56286

Reaction equation

HRID 56286 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][C:13]1=[O:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][C:13]1=[O:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 669533-MorpholinoneHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 231053824-(2-Fluoro-4-nitrophenyl)morpholin-3-oneYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1,2-difluoro-4-nitrobenzene (7.95 g, 50.0 mmol), morpholin-3-one (5.06 g, 50.0 mmol) and K2CO3 (13.82 g, 100 mmol) in DMF (80 mL) was stirred at 140° C. overnight. The mixture was cooled to rt and filtered and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=3:1) to give the title compound as a yellow solid (5.00 g, 42%).

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=3:1)

Sources & evidence

ORD record
ord-0f6ede62165a4a7eb45a4e1fb1e3c955
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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