Réaction #2166533

Équation de réaction

4-chloro-2-(2-chloro-6-methoxyphenyl)quinazoline

BBr3

→

3-chloro-2-(4-chloroquinazolin-2-yl)phenol

Rendement 60.0%

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Autrethe reaction mixture was quenched with aqueous NaHCO3 to pH 7
2. 2
   Autrethe layers were separated
3. 3
   Extractionthe aqueous layer was extracted with CH2Cl2
4. 4
   SéchageThe combined organic extracts were dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutrePurification via silica gel chromatography

Mode opératoire

To a solution of 4-chloro-2-(2-chloro-6-methoxyphenyl)quinazoline (0.3 g, 0.98 mmol) in CH2Cl2 at −78° C. was added 5 equivalents of 1 M BBr3 solution (4.9 mL, 4.9 mmol) in CH2Cl2. The reaction was complete after 30 minutes After allowing it to warm to room temperature, the reaction mixture was quenched with aqueous NaHCO3 to pH 7, the layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered, and concentrated. Purification via silica gel chromatography using 2:1 CH2Cl2:hexanes yielded 3-chloro-2-(4-chloroquinazolin-2-yl)phenol (0.17 g, 60%). LC/MS: m/z 291.1 (M+H)+ at 3.16 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Source