Morpholine → 4-(2-Bromo-4-nitrophenyl)morpholine

HRID 1713814Notes

Reaction equation

HRID 1713814 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1F>C(#N)C>[Br:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 696992-Bromo-1-fluoro-4-nitrobenzene

Product 1

HCID 27658874-(2-Bromo-4-nitrophenyl)morpholineYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Morpholine (7.92 mL, 90.9 mmol) was added to a solution of 2-bromo-1-fluoro-4-nitrobenzene (10 g, 45.5 mmol) in acetonitrile (100 mL) and the mixture was heated under reflux for 6 h. Volatile material was removed by evaporation and the residue was diluted with water (100 mL) then extracted with ethyl acetate (2×100 mL). The organic extracts were combined, dried and concentrated to give the title compound (12.9 g, 99%) as a solid; 1H NMR δ 8.40 (1H, s), 8.20 (1H, d), 7.10 (1H, d), 3.80-3.70 (4H, m), 3.20-3.10 (4H, m); MS m/e MH+ 287.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 h
  3. customVolatile material was removed by evaporation
  4. additionthe residue was diluted with water (100 mL)
  5. extractionthen extracted with ethyl acetate (2×100 mL)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2f3baa26713c459a96132afbf04ea925
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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