Ethyl bromoacetate → ethyl N-(4-fluorophenyl)glycine

HRID 5818

Reaction equation

HRID 5818 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15]1OCCOCCOCCOCCOCCO[CH2:16]1.C([O:35][C:36](=[O:39])[CH2:37]Br)C>C(O)C>[CH2:15]([N:6]([C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:37][C:36]([OH:39])=[O:35])[CH3:16]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 97314-FluoroanilineHCID 11430Potassium CarbonateHCID 2855718-Crown-6

Product 1

HCID 61998283ethyl N-(4-fluorophenyl)glycine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Fluoroaniline (5 g), potassium carbonate (3.11 g) and a catalytic amount of 18-Crown-6 were stirred together in 50 ml of ethanol. A solution of ethylbromoacetate (7.52 g) in 25 ml of ethanol was added dropwise and the reaction was heated to reflux.

Workup

  1. temperaturethe reaction was heated to reflux

Sources & evidence

ORD record
ord-d5edec4fc25d4165a206856d008fcc0a
Source dataset
uspto-grants-1993_09
Patent number
US05246933

Linked notes

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