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

HRID 541953Notes

Reaction equation

HRID 541953 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>CN(C)C=O.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 696992-Bromo-1-fluoro-4-nitrobenzene

Product 1

HCID 27658874-(2-Bromo-4-nitrophenyl)morpholineYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 2-bromo-1-fluoro-4-nitrobenzene (0.94 g, 4.3 mmol) in N,N-dimethylformamide (10 mL) was treated with potassium carbonate (1.5 g, 11 mmol) followed by morpholine (0.56 mL, 6.4 mmol) and stirred at 20° C. for 3 h. The reaction mixture was diluted with sodium bicarbonate and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and evaporated to give the desired product (1.0 g, quantitative) which was used without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-fafc83ac3fef4f6f8fd3ead7125c452f
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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