4-Iodoanisole → 1-(4'-Methoxy-2-nitro-[1,1'-biphenyl]-4-yl)ethanone

HRID 918127

Reaktionsgleichung

I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21]>[Cu]>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)=[C:12]([N+:20]([O-:22])=[O:21])[CH:13]=1)(=[O:19])[CH3:18]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A stirred mixture of 4-iodoanisole (174.5 g.), 4'-bromo-3'-nitroacetophenone (162.5 g.) and copper powder (144 g.) was heated at 80°C. for 5 hours and the temperature was then gradually raised during 4 hours to 110°C. The stirred mixture was maintained at 110°C. for a further period of 3 days. The reaction mixture was cooled to room temperature and extracted with methylene dichloride. The extract was filtered and the filtrate evaporated under reduced pressure to remove methylene dichloride. The residue was distilled in vacuo to give the product, b.p. 200° - 210°C./0.6 mm., which solidified on cooling. This product was recrystallized from methanol to give 4-acetyl-4'-methoxy-2-nitrobiphenyl, m.p. 127° - 129°C. (novel intermediate A).

Aufarbeitung

temperaturethe temperature was then gradually raised during 4 hours to 110°C
temperatureThe stirred mixture was maintained at 110°C. for a further period of 3 days
temperatureThe reaction mixture was cooled to room temperature
extractionextracted with methylene dichloride
filtrationThe extract was filtered
customthe filtrate evaporated under reduced pressure
customto remove methylene dichloride
distillationThe residue was distilled in vacuo
customto give the product, b.p. 200° - 210°C./0.6 mm
temperatureon cooling
customThis product was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag: ord-b40cd95393ac415f8610004776c1cfed
Quelldatensatz: uspto-grants-1976_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US03969402

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