Propanedioic acid, 2-(5-chloro-2,4-dinitrophenyl)-, 1-(1,1-dimethylethyl) 3-ethyl ester → HCID 86661369, compound

HRID 1773533Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:26])[CH:5]([C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24])C(OC(C)(C)C)=O)[CH3:2]>ClCCl.FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 2-(5-chloro-2,4-dinitro-phenyl)-malonic acid tert-butyl ester ethyl ester (0.4 g) in a mixture of dichloromethane (3 mL) and trifluoroacetic acid (0.5 mL) was heated at 70° C. for 30 minutes in a sealed tube. The reaction mixture was then evaporated under reduced pressure and the residue was purified by flash chromatography (EtOac/hexane, 10/90) to afford 150 mg of (5-chloro-2,4-dinitro-phenyl)-acetic acid ethyl ester.

Workup

customThe reaction mixture was then evaporated under reduced pressure
customthe residue was purified by flash chromatography (EtOac/hexane, 10/90)

Sources & evidence

ORD record: ord-c5bfd0af83d14c629b78430ca2a3ed83
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255110B2

Reaction notes

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