Sodium Carbonate → 4-Amino-6-bromo-5-hydroxy-2-methylbiphenyl-3-carbonitrile
Reaktionsgleichung
[NH2:1][C:2]1[C:7]([O:8]C)=[C:6]([Br:10])[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH3:17])[C:3]=1[C:18]#[N:19].BrB(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([Br:10])[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH3:17])[C:3]=1[C:18]#[N:19]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -70 °C
Versuchsvorschrift
4-Amino-6-bromo-5-methoxy-2-methylbiphenyl-3-carbonitrile (I-40) (44.5 mg, 0.14 mmol) was dissolved in dichloromethane (dewatered, 1.4 ml) under nitrogen atmosphere, and cooled in a dry ice-methanol bath at −70° C. 1 M Tribromoborane (dichloromethane solution, 0.42 ml) was dropwise added to it at −70 to −68° C., followed by stirring for 1.5 hours with heating up to 0° C. The reaction liquid was diluted with cold water, and controlled to have a pH of 6 to 7 with aqueous 10% sodium carbonate solution added thereto. The organic matter was extracted with ethyl acetate, washed with saturated brine, then dried on anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure to obtain the entitled compound (42.4 mg, quant.) as a pale brown solid.
Aufarbeitung
- temperaturewith heating up to 0° C
- customThe reaction liquid
- additionadded
- extractionThe organic matter was extracted with ethyl acetate
- washwashed with saturated brine
- dry with materialdried on anhydrous magnesium sulfate
- customthe solvent was evaporated away under reduced pressure
- customto obtain the entitled compound (42.4 mg, quant.) as a pale brown solid
Quellen und Nachweise
- ORD-Eintrag
- ord-56883343fbf749ceb6d67d2ae4f68704
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07737166B2
Notizen zur Reaktion
Wird geladen…