Boron tribromide → HCID 59627687, Verbindung
Reaktionsgleichung
B(Br)(Br)Br.[Cl:5][C:6]1[C:7]([O:19]C)=[CH:8][C:9]([CH3:18])=[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=1>ClCCl>[Cl:5][C:6]1[C:7]([OH:19])=[CH:8][C:9]([CH3:18])=[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Boron tribromide (1.068 mL, 11.30 mmol) was added dropwise to ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)acetate (Intermediate 3-4; 456 mg, 1.88 mmol) in dichloromethane (10 mL) at ambient temperature under nitrogen. The resulting orange red solution was stirred at 0° C. for 45 minutes. The reaction mixture was carefully quenched with water (25 mL), extracted with EtOAc (2×100 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford crude product as a yellow gum. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford ethyl 2-(5-chloro-4-hydroxy-2-methylphenyl)acetate (310 mg, 72.2%) as a colourless oil which solidified on standing.
Aufarbeitung
- customThe reaction mixture was carefully quenched with water (25 mL)
- extractionextracted with EtOAc (2×100 mL)
- dry with materialthe organic layer was dried over MgSO4
- filtrationfiltered
- customevaporated
- customto afford crude product as a yellow gum
- customThe crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane
- customPure fractions were evaporated to dryness
Quellen und Nachweise
- ORD-Eintrag
- ord-55e2275b12ac4ae59fe69811b0132e46
- Quelldatensatz
- uspto-grants-2012_05
- Patentnummer
- US08188092B2
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