Isoquinoline → 5-Bromoisoquinoline

Temperature

75 °C

The apparatus was a 500 mL three-necked flask equipped with a condenser, dropping funnel, and a stirrer terminating in a stiff, crescent-shaped Teflon polytetrafluroethylene paddle. To the isoquinoline (57.6 g, 447 mmol) in the flask was added AlCl3 (123 g, 920 mmol). The mixture was heated to 75–85° C. Bromine (48.0 g, 300 mmol) was added using a dropping funnel over a period of 4 hours. The resulting mixture was stirred for one hour at 75° C. The almost black mixture was poured into vigorously hand-stirred cracked ice. The cold mixture was treated with sodium hydroxide solution (10 N) to dissolve all the aluminum salts as sodium aluminate and the oily layer was extracted with ether. After being dried with Na2SO4 and concentrated, the ether extract was distilled at about 0.3 mm. A white solid (16.3 g, 78 mmol) from a fraction of about 125° C. was obtained (26% yield). The product was further purified by recrystallization (pentane or hexanes): mp 80–81° C.;

1. customequipped with a condenser
2. customterminating in a stiff, crescent-shaped Teflon polytetrafluroethylene paddle
3. temperatureThe mixture was heated to 75–85° C
4. customof 4 hours
5. additionThe almost black mixture was poured
6. stirringinto vigorously hand-stirred
7. extractionthe oily layer was extracted with ether
8. dry with materialAfter being dried with Na2SO4
9. concentrationconcentrated
10. extractionthe ether extract
11. distillationwas distilled at about 0.3 mm

ORD record

ord-b9469d6f4a4846c6b2874fbf0254c2dd

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091212B2