7-broMo-8-chloroquinoline synthesis

Yield:1429790-80-6 96%

Reaction Conditions:

with sulfuric acid;sodium 3-nitrobenzenesulfonate in water at 137; for 2 h;

Steps:

20.a 7-bromo-8-chloroquinoline

A 250 mL round bottom flask equipped with a stirbar and condenser was charged with 3-bromo-2-chloroaniline (0.867 g, 4.20 mmol), 3-nitrobenzenesulfonate sodium salt (1.686 g, 7.49 mmol), and propane-1,2,3-triol (1.083 g, 11.76 mmol). The mixture was then taken up in water (0.737 mL) and then carefully treated with concentrated sulfuricacid (1.363 mL). The reaction mixture was then heated to i37 °C with stirring for 2 h. The reaction mixture was then cooled to room temperature and the flask fitted with an ice bath. The mixture was then carefully adjusted to basic pH with saturated aq sodium bicarbonate. The mixture was then allowed to stir for 20 mm and then diluted with water (200 mL) and dichloromethane (200 mL). The entire mixture was then transferred to a iseparatory funnel. The organic layer was isolated and the aqueous re-extracted with an additional quantity of dichloromethane (~100 mL). The organics were then pooled, dried over sodium sulfate, filtered, and concentrated to afford the title compound as a dark brown solid (1.081 g, 4.01 mmol, 96% yield). MS(ES)+ m/e 242.1 [M+H]+.

References:

WO2013/52716,2013,A1 Location in patent:Page/Page column 57