Hydrochloric Acid → 4-(3-Bromo-4-methoxy-phenyl)-2-(4-cyano-2-nitro-phenyl)-4-methyl-3-oxo-pentanoic acid ethyl ester

HRID 61812

Reaction equation

[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6](=[O:19])[C:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([Br:18])[CH:11]=1)([CH3:9])[CH3:8])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=1[N+:36]([O-:38])=[O:37].Cl>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=1[N+:36]([O-:38])=[O:37])[C:6](=[O:19])[C:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([Br:18])[CH:11]=1)([CH3:9])[CH3:8])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

4-(3-Bromo-4-methoxy-phenyl)-4-methyl-3-oxo-pentanoic acid ethyl ester (Compound K3, 10.3 g, 30.01 mmol) was dissolved in DMF (80 mL), added with cesium carbonate (24.4 g, 2.5 eq.) and 4-chloro-3-nitro-benzonitrile (7.12 g, 1.3 eq.), and then stirred at 45° C. for 4 hr. The reaction solution was added to 1 N aqueous solution of hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration, and after concentration under reduced pressure the title compound was obtained as a crude product (yellow oily substance).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over sodium sulfate
customThe drying agent was removed by filtration
concentrationafter concentration under reduced pressure the title compound

Sources & evidence

ORD record: ord-44454808dd70496f96a693021480053d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Linked notes

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