Ethyl bromoacetate → Glycine, N-(4-chlorophenyl)-, ethyl ester

HRID 902864

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

4-Chloroaniline (2.0 g) was dissolved in acetonitrile (20 ml), and ethyl bromoacetate (2.1 g) and potassium carbonate (2.2 g) were added to stir the mixture at 60° C. for 2 days. The reaction mixture was filtered through Celite pad, and the filtrate was concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel (hexane:chloroform=2:1) to obtain the title compound (2.3 g).

Workup

filtrationThe reaction mixture was filtered through Celite pad
concentrationthe filtrate was concentrated under reduced pressure
customThe resultant residue was purified by column chromatography on silica gel (hexane:chloroform=2:1)

Sources & evidence

ORD record: ord-5ec36d3d26a1439cae354690b211cd5c
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365205B2

Linked notes

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