Boron tribromide → 1-(Hydroxymethyl)-3-methylenecyclobutane-1-carbonitrile
Reaktionsgleichung
C[O:2][CH2:3][C:4]1([C:9]#[N:10])[CH2:7][C:6](=[CH2:8])[CH2:5]1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][CH2:3][C:4]1([C:9]#[N:10])[CH2:7][C:6](=[CH2:8])[CH2:5]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a mixture of 1-(methoxymethyl)-3-methylenecyclobutanecarbonitrile (1.40 g, 0.0102 mol) in methylene chloride (30 mL, 0.4 mol) was added 1.0 M of boron tribromide in methylene chloride (12.8 mL) at −78° C. The reaction was stirred at rt for 2 h, quenched with aq. sodium bicarbonate, and extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate and evaporated to dryness to give the desired product (1.26 g, 100%). 1H NMR (400 MHz, CDCl3): 4.81 (2H, m), 3.66 (2H, s), 3.10 (2H, m), 2.59 (2H, m) ppm.
Aufarbeitung
- customquenched with aq. sodium bicarbonate
- extractionextracted with dichloromethane
- dry with materialThe combined organic layers were dried over magnesium sulfate
- customevaporated to dryness
Quellen und Nachweise
- ORD-Eintrag
- ord-c5c89c19f1cd462ab058ce4730882127
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08158616B2
Notizen zur Reaktion
Wird geladen…