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

HRID 618343Notes

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. ##STR62##

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-ac63ff0353a44b1bb8906f21ba8bed41
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05952368

Reaction notes

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