Morpholine → 4-(2-Bromo-5-methyl-4-nitrophenyl)morpholine

HRID 541564Notes

Reaction equation

HRID 541564 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][C:3]=1F.C(=O)([O-])[O-].[K+].[K+].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]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])[C:5]([CH3:11])=[CH:4][C:3]=1[N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 27793654-Bromo-5-fluoro-2-nitrotoluene

Product 1

HCID 579616454-(2-Bromo-5-methyl-4-nitrophenyl)morpholineYield 77.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-Bromo-2-fluoro-4-methyl-5-nitrobenzene (1.0 g, 4.3 mmol) [Aldrich] was stirred in N,N-dimethylformamide (10 mL) with potassium carbonate (1.5 g, 11.0 mmol), and morpholine (0.56 mL, 6.4 mmol) was added. The mixture was stirred for 3 hours and diluted with saturated sodium bicarbonate solution. Extraction with ethyl acetate gave the desired compound (1.0 g, 77%). LCMS for C11H14BrN2O3 (M+H)+: m/z=301.0.

Workup

  1. additionwas added
  2. extractionExtraction with ethyl acetate

Sources & evidence

ORD record
ord-3ce0695bae724a08b8daf95c397a3ecb
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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