Carbon Tetrachloride → 4-(4-Methoxyphenyl)-benzofuran-7-carbaldehyde

HRID 1372159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372159
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]3[CH:15]=[CH:16][O:17][C:13]=3[C:12]([CH3:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(Cl)(Cl)(Cl)Cl.C1C(=O)N(Br)C(=[O:27])C1.OP([O-])([O-])=O.[K+].[K+]>CC(N=NC(C#N)(C)C)(C#N)C.CC#N>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:14]3[CH:15]=[CH:16][O:17][C:13]=3[C:12]([CH:18]=[O:27])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Komponenten

7

Edukt 4

HCID 5943Carbon TetrachlorideHCID 24450Potassium Phosphate, DibasicHCID 67184N-bromobutanimideHCID 210717824-(4-Methoxyphenyl)-7-methylbenzofuran

Produkt 1

HCID 210717834-(4-Methoxyphenyl)-benzofuran-7-carbaldehydeAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a 250 ml round bottom flask was added 4-(4-methoxyphenyl)-7-methylbenzofuran (600 mg, 2.52 mmol), CCl4 (70 ml), NBS (490 mg, 2.77 mmol), and a catalytic amount of AIBN (25 mg). The reaction was brought to reflux for 2 h after which the reaction was allowed to cool, the solids were filtered off, and the solution concentrated. CH3CN (30 ml), K2HPO4 (440 mg, 2.53 mmol), and potassium benzeneselenite (630 mg, 2.77 mmol) were added and the reaction was brought to reflux for 2 h after. The reaction was cooled, passed through a silica plug (washed with 30% EtOAc/hex.), and concentrated to 810 mg of an orange solid. Further purification by chromatography (100% CH2Cl2) afforded 500 mg (78%) of product as a tan colored solid: mp 104–105° C.; 1H NMR (500 MHz, DMSO-d6): δ 3.85 (3H, s), 7.14 (2H, d, J=8.8 Hz), 7.20 (1H, d, J=2.2 Hz), 7.56 (1H, d, J=8.0 Hz), 7.69 (2H, d, J=8.8 Hz), 7.91 (1H, d, J=7.7 Hz), 8.26 (1H, d, J=2.2 Hz), 10.36 (1H, s); HRMS (ESI+) m/z 253.08622 ([M+H]+).

Aufarbeitung

  1. temperatureto reflux for 2 h after which the reaction
  2. temperatureto cool
  3. filtrationthe solids were filtered off
  4. concentrationthe solution concentrated
  5. temperatureto reflux for 2 h after
  6. temperatureThe reaction was cooled
  7. concentrationconcentrated to 810 mg of an orange solid
  8. customFurther purification by chromatography (100% CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-3887411548a448ff899ea3c9cd148000
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157491B2

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