Potassium Carbonate → Methyl 3-(5-bromo-2-nitrophenylamino)-2-methylpropanoate

HRID 1485419Notes

Reaction equation

HRID 1485419 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][CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16].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][CH:14]([CH3:19])[C:15]([O:17][CH3:18])=[O:16])[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27833624-Bromo-2-fluoro-1-nitrobenzeneHCID 10486829Methyl 3-amino-2-methylpropanoate

Product 1

HCID 70978426Methyl 3-(5-bromo-2-nitrophenylamino)-2-methylpropanoateYield 59.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (9.4 g, 42.7 mmol) in tetrahydrofuran (100 mL) were added methyl 3-amino-2-methylpropanoate (5 g, 42.7 mmol) and potassium carbonate (11.8 g, 85.4 mmol). The reaction mixture was stirred with refluxing for 3 hours. The mixture was diluted with water (100 mL), extracted with ethyl acetate (100 mL×3). The organic layers were separated, combined, dried over anhydrous sodium sulfate, filtered and concentrated to give a residue, which was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give methyl 3-(5-bromo-2-nitrophenylamino)-2-methylpropanoate as a light yellow solid (8 g, 59%).

Workup

  1. temperaturewith refluxing for 3 hours
  2. extractionextracted with ethyl acetate (100 mL×3)
  3. customThe organic layers were separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue, which
  8. customwas purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-caf2c39d03bf482e9ecb88d4b4c883bf
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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