Morpholine → 4-(2,6-Difluoro-4-nitrophenyl)morpholine

HRID 56297Notes

Reaction equation

HRID 56297 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1F.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.CCN(CC)CC>CCOC(C)=O>[F:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([F:1])[C:3]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 223856304-(2,6-Difluoro-4-nitrophenyl)morpholineYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1,2,3-trifluoro-5-nitrobenzene (3.54 g, 20.0 mmol), morpholine (2.0 mL, 23.0 mmol) and Et3N (8.5 mL, 61.0 mmol) in EtOAc (30 mL) was stirred at rt for 5 h. The mixture was concentrated in vacuo, and the residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1) to give the title compound as a yellow solid (4.76 g, 98%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=8:1)

Sources & evidence

ORD record
ord-04fd99919e6944dd9f0003da4c38a39a
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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