1-Bromo-2-nitrobenzene → 2-(2-Nitrophenyl)furan

HRID 1816283

Reaktionsgleichung

Reaktionsgleichung von HRID 1816283
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1Br)([O-:3])=[O:2].C([Sn](CCCC)(CCCC)[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)CCC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 2

HCID 113411-Bromo-2-nitrobenzeneHCID 43936882-(Tributylstannyl)furan

Produkt 1

HCID 123772252-(2-Nitrophenyl)furanAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A DMF solution of 2-nitrobromobenzene (2.02 g), 2-tributylstannylfuran (3.31 mL), and tetrakis(triphenylphosphine)palladium was heated at 97° C. under N2 overnight. The mixture was evaporated to a small volume. The residue was suspended in 40 mL of water. This mixture was extracted with two 50 mL portions of Et2O. The combined extracts were dried and evaporated. This oil was purified by chromatography on silica gel with 10% EtOAc/hexanes to yield 0.51 g (27%) of 2-(2-nitrophenyl)furan. [This compound was reported in Smith et al.; J. Am. Chem. Soc. 1953, 75, 6335.]

Aufarbeitung

  1. customThe mixture was evaporated to a small volume
  2. extractionThis mixture was extracted with two 50 mL portions of Et2O
  3. customThe combined extracts were dried
  4. customevaporated
  5. customThis oil was purified by chromatography on silica gel with 10% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3261a5a25f3f4ce8b425debab6f21333
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884801B1

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