Hydrochloric Acid → 5-bromo-6-methyl-1H-indole

HRID 1754962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1754962
COC(=O)[NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:6]=1[C:13]#[C:14][Si](C)(C)C.[O-]CC.[Na+].Cl>C(O)C.[Cl-].[Na+].O>[Br:12][C:8]1[CH:7]=[C:6]2[C:5](=[CH:10][C:9]=1[CH3:11])[NH:4][CH:14]=[CH:13]2

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 66816224(4-Bromo-5-methyl-2-trimethylsilanylethynyl-phenyl)-carbamic acid methyl ester

Produkt 1

HCID 247292415-bromo-6-methyl-1H-indoleAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(4-Bromo-5-methyl-2-trimethylsilanylethynyl-phenyl)-carbamic acid methyl ester (506 mg, 1.49 mmol) was dissolved in ethanol (6 ml). Sodium ethoxide (20% solution in ethanol, 1.17 ml, 2.97 mmol) was added and the mixture was stirred at 70° C. overnight. The reaction solution was poured into ice water, and 1 N hydrochloric acid and saturated brine were added to this mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to give 5-bromo-6-methyl-1H-indole (207 mg, 66%).

Aufarbeitung

  1. additionwere added to this mixture
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ffee61e408fd43899e86637587047854
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169254B2

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