Triphenylphosphine → 3-(Bromomethyl)-1-benzofuran
Reaktionsgleichung
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.O[CH2:23][C:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH:25]=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:23][C:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH:25]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a stirring solution of 912 mg (3.48 mmol, 1.2 equiv) of triphenylphosphine in 5 mL of CCl4 at 0° C. is added 165 μL (3.19 mmol, 1.1 equiv) of Br2. The resulting orange-yellow suspension is stirred 10 min at 0° C., then a solution of 430 mg (2.90 mmol) of 3-hydroxymethylbenzofuran, prepared as in Intermediate 19, in 5 mL of CCl4 is added over 2 min. The resulting solution is stirred 1.5 h at RT, and the solvent is removed in vacuo. Purification of the residue by silica gel flash column chromatography using hexane/EtOAc 20/1 as eluent afforded 500 mg of the title compound as a clear, colorless oil: 1H NMR (CDCl3, 300 MHz) δ7.71 (m, 2H), 7.50 (m, 1H), 7.37 (m, 2H), 4.62 (s, 2H); Rf =0.67 in hexane/EtOAc 5/1.
Aufarbeitung
- stirringThe resulting solution is stirred 1.5 h at RT
- customthe solvent is removed in vacuo
- customPurification of the residue by silica gel flash column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-9b3f772a1a524a8189d352fe031a8f49
- Quelldatensatz
- uspto-grants-1999_01
- Patentnummer
- US05859007
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