Morpholine → 4-(3-Fluoro-4-nitrophenyl)morpholine

HRID 1768110Notes

Reaction equation

HRID 1768110 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C1COCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:7]=1.[F:1][C:2]1[CH:7]=[C:6]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 679672,4-Difluoronitrobenzene

Product 2

HCID 222807594-(3-Fluoro-4-nitrophenyl)morpholineHCID 22280782HCID 22280782, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,4-difluoronitrobenzene (10.0 mL) and morpholine (17.4 mL) in THF (100 mL) was stirred at RT under N2 for 2 h. The solvent was removed and the residue was partitioned between EtOAc and water. The organic layer was washed brine, dried over MgSO4, and concentrated. The resulting solid was purified by chromatography on silica gel with 20–50% EtOAc in hexane to give 18.1 g of 4-fluoro-2-morpholinonitrobenzene and 1.81 g of 2-fluoro-4-morpholinonitrobenzene. ESI mass spectrum z (rel. intensity) 227.1 (M+H, 100).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between EtOAc and water
  3. washThe organic layer was washed brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting solid was purified by chromatography on silica gel with 20–50% EtOAc in hexane

Sources & evidence

ORD record
ord-10b8e372966a444e821d904222650501
Source dataset
uspto-grants-2007_06
Patent number
US07235575B2

Reaction notes

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