p-Fluoronitrobenzene → Methyl 2-(1-methylpyrrol-2-yl)-2-(4-nitrophenyl)acetate

HRID 365627Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([O:10][CH3:11])=[O:9].F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.[H-].[Na+]>CN(C=O)C>[CH3:11][O:10][C:8](=[O:9])[CH:7]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 1-methylpyrrole-2-acetate (5.32 g, 34.73 mmol) and 4-fluoro-nitrobenzene (4.9 g, 34.73 mmol) were dissolved in dry DMF (100 ml), and the solution was cooled to 0° C. under nitrogen. Sodium hydride powder (1.75 g, 72.93 mmol) was added in portions. After 30 min the reaction mixture was quenched with 1 M HCl and the product was extracted into ether. The organic extracts were washed with water and brine, and dried over magnesium sulfate. The solvent was removed in vacuo to give methyl-2-(1-methylpyrrol-2-yl)-2-(4-nitrophenyl)acetate (9.20 g, 97%) as a red oil. ##STR61##

Workup

customAfter 30 min the reaction mixture was quenched with 1 M HCl
extractionthe product was extracted into ether
washThe organic extracts were washed with water and brine
dry with materialdried over magnesium sulfate
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-b6b5761c5ea1477bba005406e721c3ac
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127402

Reaction notes

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