p-Fluoronitrobenzene → HCID 22989696, compound

HRID 1168741Notes

Reaction equation

HRID 1168741 reaction equation
Cl.[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].[N+:11]([C:14]1[CH:19]=[CH:18][C:17](F)=[CH:16][CH:15]=1)([O-:13])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:2]([O:6][C:7](=[O:10])[CH2:8][NH:9][C:17]1[CH:18]=[CH:19][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 22989696HCID 22989696, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of glycine tert-butyl ester hydrochloride (3.35 g, 20 mmol), 4-nitrofluorobenzene (2.82 g, 20 mmol) and potassium carbonate (4.2 g, 30 mmol) in DMSO (15 mL) was heated at 90° C. for 22 hr. The reaction mixture was allowed to cool to room temperature and then poured onto crushed ice. The precipitated yellow solid was filtered, washed with water and dried (Na2SO4) to give N-(4-nitrophenyl)glycine tert-butyl ester (4.1 g, 81%).

Workup

  1. temperatureto cool to room temperature
  2. additionpoured
  3. customonto crushed ice
  4. filtrationThe precipitated yellow solid was filtered
  5. washwashed with water
  6. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-9089c712db564717881c89e7ea5b5e7d
Source dataset
uspto-grants-2003_09
Patent number
US06627647B1

Reaction notes

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