Potassium Carbonate → Ethyl 1-((5-bromo-2-nitrophenylamino)methyl)cyclopropanecarboxylate

HRID 1485427Notes

Reaction equation

HRID 1485427 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[NH2:12][CH2:13][C:14]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:12][CH2:13][C:14]2([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]2)[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27833624-Bromo-2-fluoro-1-nitrobenzeneHCID 11480505Ethyl 1-(aminomethyl)cyclopropanecarboxylate

Product 1

HCID 70978279Ethyl 1-((5-bromo-2-nitrophenylamino)methyl)cyclopropanecarboxylateYield 80.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (792 mg, 3.6 mmol) in tetrahydrofuran (30 mL) was added ethyl 1-(aminomethyl)cyclopropanecarboxylate (441 mg, 3.0 mmol) and potassium carbonate (621 mg, 4.5 mmol). The reaction mixture was stirred at reflux for 15 hours. The mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL). The organic phase was separated, concentrated and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give ethyl 1-((5-bromo-2-nitrophenylamino)methyl)cyclopropanecarboxylate as a light yellow solid (832 mg, 67%).

Workup

  1. temperatureat reflux for 15 hours
  2. extractionextracted with ethyl acetate (50 mL)
  3. customThe organic phase was separated
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-3a1ca6b6756441bc8b51c6573ea4ae62
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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