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

HRID 2275188

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-b9a77d65ee814fd19aab8bbb02a51c66
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126931B2

Linked notes

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