5-Bromo-2-chloroisonicotinic acid → (5-Bromo-2-chloropyridin-4-yl)methanol

A 0° C. solution of 5-bromo-2-chloroisonicotinic acid (5.008 g, 21.18 mmol) in THF (30 mL) was treated with borane tetrahydrofuran complex (52.9 ml, 52.9 mmol). The solution was stirred at room temperature for 16 hours. The reaction was slowly quenched with water until gas formation stopped. Then 25 mL of 3 N NaOH was added and the resulting mixture was heated in a 100° C. oil bath for about 75 minutes. The reaction was cooled and the volatiles removed by rotary evaporation. Ethyl acetate and brine were added, after which the layers were separated. The organic was dried over Na2SO4, filtered and the filtrate concentrated and dried to give a yellow solid that was used without further purification. 1H NMR (CDCl3, 500 MHz): δ 8.41 (s, 1H), 7.58 (s, 1H), 4.74 (s, 2H), 2.23 (br, 1H).

1. customThe reaction was slowly quenched with water until gas formation
2. additionThen 25 mL of 3 N NaOH was added
3. temperaturethe resulting mixture was heated in a 100° C. oil bath for about 75 minutes
4. temperatureThe reaction was cooled
5. customthe volatiles removed by rotary evaporation
6. additionEthyl acetate and brine were added
7. customafter which the layers were separated
8. dry with materialThe organic was dried over Na2SO4
9. filtrationfiltered
10. concentrationthe filtrate concentrated
11. customdried
12. customto give a yellow solid that
13. customwas used without further purification

ORD record

ord-2d8be14debdd448c8f2f7a4580f89c1e

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353101B2