Phosphorus tribromide → tert-butyl 4-(bromomethyl)-1H-indole-1-carboxylate

HRID 11748

Reaktionsgleichung

Reaktionsgleichung von HRID 11748
P(Br)(Br)[Br:2].[C:5]([N:12]1[C:20]2[C:15](=[C:16]([CH2:21]O)[CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1)([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C([O-])(O)=O.[Na+]>CCOCC.C(Cl)Cl>[Br:2][CH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[CH:14]=[CH:13][N:12]2[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Komponenten

6

Edukt 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 12148524tert-Butyl 4-(hydroxymethyl)-1H-indole-1-carboxylate

Produkt 1

HCID 12148525tert-butyl 4-(bromomethyl)-1H-indole-1-carboxylateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

PBr3 (2.4 mL. 25.8 mmol) was added dropwise at 0° C. under nitrogen to a stirred solution of tert-butyl 4-(hydroxymethyl) 1H-1-indolecarboxylate 6 (6.0 g, 24.3 mmol) in ether (80 mL) and CH2Cl2 (20 mL) under nitrogen. The reaction was completed 30 minutes after the addition. The mixture was poured into a cold aqueous NaHCO3 solution (100 mL) and extracted with ethyl acetate (3×80 mL). The combined extract was washed sequentially with water (80 mL), and brine (80 mL), then dried (MgSO4), filtered, and finally concentrated to provide tert-butyl 4-(bromomethyl)-1H-1-indolecarboxylate 7 (6.3 g, 84%) as an oil which was immediately taken to the next step.

Aufarbeitung

  1. additionafter the addition
  2. extractionextracted with ethyl acetate (3×80 mL)
  3. extractionThe combined extract
  4. washwas washed sequentially with water (80 mL), and brine (80 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationfinally concentrated

Quellen und Nachweise

ORD-Eintrag
ord-5f42e2530e154a3096b9b9ddf20e8732
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098307B2

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