Reaktion #1435751

Reaktionsgleichung

2-bromo-1-(3-methoxy-phenyl)-ethanone

boron tribromide

→

2-Bromo-1-(3-hydroxy-phenyl)-ethanone

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with ice water
2. 2
   Sonstigethe organic layer was separated
3. 3
   ExtraktionThe aqueous layer was extracted with EtOAc
4. 4
   Trocknendried with sodium sulfate
5. 5
   SonstigeRemoval of solvent
6. 6
   Sonstigegave a greenish solid which
7. 7
   Sonstigewas purified by chromatography (EtOAc/Hexane, 25%)
8. 8
   Sonstigegave an off-white solid

Vorschrift

To a stirred solution of 2-bromo-1-(3-methoxy-phenyl)-ethanone (Aldrich, 3.44 g, 15 mmol) in methylene chloride (20 mL) at −10° C., boron tribromide (Aldrich, 16.5 mmol, 1M solution in CH2Cl2, 16.5 mL) was added slowly and the mixture was stirred for 1.5 hours. The reaction was quenched with ice water and the organic layer was separated. The aqueous layer was extracted with EtOAc and the extracts were combined and dried with sodium sulfate. Removal of solvent gave a greenish solid which was purified by chromatography (EtOAc/Hexane, 25%) gave an off-white solid. 770 mg, 24%. The compound was used directly for the next step.

Quelle