Indole → 1-Phenyl-1H-indole

HRID 5594

Reaktionsgleichung

Reaktionsgleichung von HRID 5594
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[C:11]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 798IndoleHCID 6228DimethylformamideHCID 7961BromobenzeneHCID 11430Potassium Carbonate

Produkt 1

HCID 1820291-Phenyl-1H-indoleAusbeute 20,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 17.57 g (0.15 mole) of indole, 23.55 g (0.15 mole) of bromobenzene, 21 g of anhydrous potassium carbonate, 0.75 g of CuO, and 30 mL of DMF was stirred and heated under reflux for 43 hours. The cooled mixture was diluted with 200 mL of H2O and extracted with 150 mL of ether. The extract was washed with H2O (2×50 mL) and 50 mL of brine and dried over MgSO4. The oil was chromatographed on the solvent left 35.7 g of brown oil. The oil was chromatographed on a 1100 g column of silica gel. The column was eluted with 25% CH2Cl2 -Skellysolve B and 200 mL fractions were collected. The fractions were assayed by silica gel tlc (1×4") (25% CH2Cl2 -Skellysolve B). Fractions 15-22 were combined giving 5.86 g (20%) of 1-phenylindole as a yellow oil.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 43 hours
  3. extractionextracted with 150 mL of ether
  4. washThe extract was washed with H2O (2×50 mL) and 50 mL of brine
  5. dry with materialdried over MgSO4
  6. customThe oil was chromatographed on the solvent
  7. waitleft 35.7 g of brown oil
  8. customThe oil was chromatographed on a 1100 g column of silica gel
  9. washThe column was eluted with 25% CH2Cl2 -Skellysolve B and 200 mL fractions
  10. customwere collected

Quellen und Nachweise

ORD-Eintrag
ord-9e54ac87e6cd4333953c4b9787bd6f06
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245046

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