Isoquinoline → 5-Bromoisoquinoline

Temperature

80 °C

The apparatus consisted of 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 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 a vigorously hand-stirred cracked ice. The cold mixture was treated with sodium hydroxide solution (10N) 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 1.25° C. was obtained (26% yield). The product was further purified by recrystallization (pentane or hexanes): mp 80-81° C.;

1. customThe apparatus consisted of a 500 mL three-necked flask
2. customequipped with a condenser
3. customterminating in a stiff, crescent-shaped Teflon polytetrafluroethylene paddle
4. customof 4 hours
5. additionThe almost black mixture was poured into
6. stirringa 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-13af56eebea44e3da59642de38943367

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06645975B1