4-Bromoaniline → methyl N-(4-bromophenyl)glycinate

HRID 2219221Notes

Reaction equation

HRID 2219221 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1.Br[CH2:16][C:17]([O:19][CH3:20])=[O:18].C(OCC)(=O)C>CN(C=O)C.O>[CH3:20][O:19][C:17](=[O:18])[CH2:16][NH:12][C:11]1[CH:13]=[CH:14][C:8]([Br:7])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 78074-BromoanilineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 974071methyl N-(4-bromophenyl)glycinateYield 33.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (2.41 g, 17.4 mmol) is added to a stirred solution of 4-bromo-aniline (2.00 g, 11.6 mmol) and methyl bromoacetate (1.78 g, 11.6 mmol) in dry DMF (20 mL) at ambient temperature. The mixture is heated at 100° C. for 1 hour. At ambient temperature ethyl acetate (60 mL) and water (60 mL) are added to the mixture. The organic layer is separated, washed with half-saturated brine, dried, filtered and concentrated. After MPLC separation on silica (gradient 0-15% ethyl acetate in hexane), 0.94 g (33% yield) of the title compound is obtained. 1H NMR (DMSO-d6): δ3.62 (s, 3H), 3.87 (d, J=6.4 Hz, 2H), 6.22 (t, J=6.4 Hz, 1H), 6.49 (d, J=8.8 Hz, 2H), 7.19 (d, J=8.8 Hz, 2H).

Workup

  1. customThe organic layer is separated
  2. washwashed with half-saturated brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customAfter MPLC separation on silica (gradient 0-15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8c25c793881946dea5fba792f0b21ff2
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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