Boron tribromide → 6-Bromo-5-hydroxy-1H-indole-2-carboxylic acid ethyl ester

HRID 506762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506762
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15]C)=[C:10]([Br:17])[CH:9]=2)=[O:5])[CH3:2].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[C:10]([Br:17])[CH:9]=2)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 14546582HCID 14546582, Verbindung

Produkt 1

HCID 670179076-Bromo-5-hydroxy-1H-indole-2-carboxylic acid ethyl esterAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The solution of 8.30 g (27.8 mmol) 6-bromo-5-methoxy-1H-indole-2-carboxylic acid ethyl ester (prepared according to J. Org. Chem. 1974, 39, 3580) in 160 mL dichloromethane was cooled to −78° C. At this temperature, 55.7 mL boron tribromide (55.7 mmol; 1M solution in dichloromethane) were added. The solution was allowed to warm to room temperature and after 30 min. the solution was poured on 10% aqueous sodium bicarbonate solution, the phases were separated and the aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with water followed by brine, dried over magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel with n-hexane:ethyl:acetate (2:1 v/v) as eluant to give 5.7 g (72%) of the product as a light yellow solid.

Aufarbeitung

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was flash-chromatographed on silica gel with n-hexane:ethyl:acetate (2:1 v/v) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-a1d63c3817344f64adae53973e46548c
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786109B2

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