Benzyl Bromide → 1H-Indol-5-ol, 1-(phenylmethyl)-

HRID 3385

Reaktionsgleichung

C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.B(Br)(Br)Br.C(Cl)Cl>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:7]=[CH:6]2

Komponenten

Reaktionsbedingungen

Temperatur: -5 °C

Versuchsvorschrift

5-Methoxy-1H-indole (5.6 g, 21.5 mmol) was reacted with 1.0 g (25 mmol) of 60% sodium hydride and then 3.0 mL (25 mmol) of benzyl bromide by the method described in Example 12, Part D to give crude 5-methoxy-1-(phenylmethyl)-1H-indole. This material was dissolved in 250 mL of methylene chloride, cooled to -5° C., 50 mL of 1M BBr3 /CH2Cl2 added, the cooling bath removed and the mixture stirred for 1.75 hours. Ice water was added and the mixture stirred. The organic layer was separated, washed with saturated NaCl, dried (Na2 SO4), and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% ether/hexane→ether to give 870 mg (19% overall yield) of crude 5-hydroxy-1-(phenylmethyl)-1H-indole.

Aufarbeitung

customto give crude 5-methoxy-1-(phenylmethyl)-1H-indole
customthe cooling bath removed
additionIce water was added
stirringthe mixture stirred
customThe organic layer was separated
washwashed with saturated NaCl
customdried (Na2 SO4)
concentrationconcentrated at reduced pressure
customThe residue was chromatographed on silica gel
washeluted with 20% ether/hexane

Quellen und Nachweise

ORD-Eintrag: ord-39e0ce5ac6fe453c825a8e16562f634e
Quelldatensatz: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05733923

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