Boron tribromide → 4-(4-chlorobenzyl)-6-bromo-2-(2-hydroxyphenyl)-1,2,4-triazine-3,5(2H,4H)-dione
Reaktionsgleichung
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([Br:14])=[N:10][N:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21]C)[C:8]2=[O:23])=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([Br:14])=[N:10][N:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[OH:21])[C:8]2=[O:23])=[CH:24][CH:25]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
According to Scheme 9 Step 1: To a solution of 4-(4-chlorobenzyl)-6-bromo-2-(2-methoxyphenyl)-1,2,4-triazine-3,5(2H,4H)-dione (150 mg, 0.35 mmol) in DCM (2 ml) cooled at −78° C. was added dropwise BBr3 (0.710 mL, 0.710 mmol). The reaction mixture was stirred 1 h at −78° C. and was quenched with MeOH. The mixture was allowed to reach room temperature. Water was added and the aqueous layer was extracted with DCM (×3). The combined organic layers were successively washed with water, brine, dried over MgSO4, filtered and concentrated. 131 mg (yield=90%) of 4-(4-chlorobenzyl)-6-bromo-2-(2-hydroxyphenyl)-1,2,4-triazine-3,5(2H,4H)-dione were recovered as a beige solid which was used in the next step without any purification.
Aufarbeitung
- customwas quenched with MeOH
- customto reach room temperature
- additionWater was added
- extractionthe aqueous layer was extracted with DCM (×3)
- washThe combined organic layers were successively washed with water, brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-90f92e531b004a37993d887e756cb70d
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08779129B2
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