Chloroform → (4-Amino-3-chloro-phenyl)-acetic acid ethyl ester

HRID 913164Notes

Reaction equation

HRID 913164 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)[CH3:2].C(Cl)(Cl)[Cl:15]>>[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])=[CH:11][C:10]=1[Cl:15]

Participants

3

Reactant 2

HCID 6212ChloroformHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 17859298(4-Amino-3-chloro-phenyl)-acetic acid ethyl ester

Procedure

Ethyl-4-aminophenylacetate (20 g, 112 mmol) was dissolved in chloroform (300 ml) and treated with N-chlorosuccinimde (14.92 g, 112 mmol) and stirred for 15 minutes at room temperature under argon. Reaction mixture was washed with water, brine and dried over magnesium sulphate. Evaporated to a brown oil which was purified by chromatography on silica gel eluting with ethyl acetate (0-45%) in hexane to give the title compound as a orange oil (10.12 g, 47.4 mmol). LC/MS: Rt=2.59, [MH]+ 214.

Workup

  1. additiontreated with N-chlorosuccinimde (14.92 g, 112 mmol)
  2. customReaction mixture
  3. washwas washed with water, brine
  4. dry with materialdried over magnesium sulphate
  5. customEvaporated to a brown oil which
  6. customwas purified by chromatography on silica gel eluting with ethyl acetate (0-45%) in hexane

Sources & evidence

ORD record
ord-2458a4efd54e4335b6bb793f8d47f301
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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