Boron tribromide → Methyl 3-(3-hydroxyphenyl)benzoate
Reaktionsgleichung
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:15][O:14][C:12]([C:11]1[CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([OH:2])[CH:4]=2)[CH:18]=[CH:17][CH:16]=1)=[O:13]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a −78° C. solution of methyl 3-(3-methoxyphenyl)-benzoate (1.48 g) in anhydrous methylene chloride (16 mL) was added dropwise a solution of boron tribromide in methylene chloride (1.0 M, 16.3 mL). The mixture was stirred at −78° C. for 30 min, allowed to warm to 0° C., and stirred for 2 h. The mixture was quenched by addition of saturated aqueous sodium bicarbonate (50 mL), and diluted with methylene chloride (50 mL). The mixture was placed in a separatory funnel, and the organic layer was separated, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by silica gel chromatography (eluting with 5:1 hexanes/ethyl acetate) afforded the title compound (769 mg) as a pale yellow oil.
Aufarbeitung
- temperatureto warm to 0° C.
- stirringstirred for 2 h
- customThe mixture was quenched by addition of saturated aqueous sodium bicarbonate (50 mL)
- additiondiluted with methylene chloride (50 mL)
- customThe mixture was placed in a separatory funnel
- customthe organic layer was separated
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give the crude product
- customPurification
- washby silica gel chromatography (eluting with 5:1 hexanes/ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-a830c2bd6c4b40c98a5ea2878bb4ab03
- Quelldatensatz
- uspto-grants-2001_06
- Patentnummer
- US06251925B1
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