Boron tribromide → 4-Hydroxy-3-(2-phenylethyl)benzo[b]thiophene

HRID 230885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230885
C[O:2][C:3]1[C:11]2[C:10]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:9][S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[OH:2][C:3]1[C:11]2[C:10]([CH2:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:9][S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 231035114-Methoxy-3-(2-phenylethyl)benzo[b]thiophene

Produkt 1

HCID 231035674-Hydroxy-3-(2-phenylethyl)benzo[b]thiopheneAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-methoxy-3-(2-phenylethyl)benzo-[b]thiophene (0.77 g) in dichloromethane (25 mL) was added boron tribromide (0.54 mL) at −78° C., and the mixture was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with diethylether. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1) to give the title compound (0.66 g).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with diethylether
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1)

Quellen und Nachweise

ORD-Eintrag
ord-924567b9069b486491da325b22f6a0e5
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566699B2

Notizen zur Reaktion

Wird geladen…