Pyrrole → 3-Fluoro-1-nitro-4-(1H-pyrrol-1-yl)benzene

HRID 1955106Notes

Reaction equation

[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1F.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1[N:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1

Participants

Conditions

Temperature: 50 °C

Procedure

A slurry of 403 mg(630 mg of 60% in oil, 15.75 mmol) of sodium hydride in 85 mL THF was treated with 1.01 g(1.04 mL, 15 mmol) of pyrrole, followed by warming at 50° C. foe 15 min. The solution was then treated with 2.51 g(1.74 mL, 15.75 mmol) of 3.4-difluoronitrobenzene, followed by warming at reflux for 18h. The mixture was then cooled and treated with lOmL saturated ammonium chloride solution. The mixture was diluted with ethyl acetate and extracted with water (2×). Drying (Na2SO4) and concentration in vacuo afforded a dark brown solid, which was chromatographed over 75 g of 230-400 mesh silica gel, eluting with 30%(v/v) dichloromethane in hexane. These procedures afforded 2.05 g(66%) of the title pyrrole derivative as a light yellow solid. 1H NMR (CDCl3): δ8.14, 7.57, 7.16, 6.44.

Workup

temperatureby warming
temperatureat reflux for 18h
temperatureThe mixture was then cooled
extractionextracted with water (2×)
customDrying
concentration(Na2SO4) and concentration in vacuo
customafforded a dark brown solid, which
customwas chromatographed over 75 g of 230-400 mesh silica gel
washeluting with 30%(v/v) dichloromethane in hexane

Sources & evidence

ORD record: ord-b73cc8136b1c4bcda263313bdbae35fb
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124334

Reaction notes

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