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Boron tribromide → 6-Ethyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indol-4-ol

HRID 2421255
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2421255
[CH2:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[C:14]([F:20])[CH:13]=2)=[C:5]([O:21]C)[CH:4]=1)[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([C:3]1[CH:4]=[C:5]([OH:21])[C:6]2[CH:7]=[CH:8][N:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([F:20])[CH:13]=3)[C:10]=2[CH:11]=1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 596279376-Ethyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole

Produkt 1

HCID 441931886-Ethyl-1-(3-fluoro-4-hydroxyphenyl)-1H-indol-4-olAusbeute 4,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 6-ethyl-1-[3-fluoro-4-(methyloxy)phenyl]-4-(methyloxy)-1H-indole (D10) (180 mg, 0.60 mmol) in dichloromethane (6 mL) at −78° C. was added boron tribromide (1 M solution in dichloromethane, 2.5 mL, 2.5 mmol). The reaction mixture was allowed to warm to 0° C. and then quenched by the addition of water and dichloromethane. The solution was neutralised by the addition of dilute sodium hydrogen carbonate solution. The organic phase was separated and then the aqueous phase re-extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated at reduced pressure. The product was purified by MDAP to yield the title compound (E6), (8 mg).

Aufarbeitung

  1. customquenched by the addition of water and dichloromethane
  2. additionThe solution was neutralised by the addition of dilute sodium hydrogen carbonate solution
  3. customThe organic phase was separated
  4. extractionthe aqueous phase re-extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customThe product was purified by MDAP

Quellen und Nachweise

ORD-Eintrag
ord-b2256c0ba64f4d41bbed2ab04154f8ef
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07956083B2

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