Bromine → 2-Bromo-3-fluoro-5-(trifluoromethyl)pyridine

The 3-fluoro-5-(trifluoromethyl)-picolinic acid (7.35 g, 0.035 mole) staring material was put into 150 ml of dry carbon tetrachloride and then red mercuric oxide (9.1 g, 0.042 mole) was added and the mixture was stirred and refluxed 1 hour and 25 minutes. A solution of bromine (6.7 g, 0.042 mole) in 20 ml of dry carbon tetrachloride was added slowly with the mixture at reflux over the next 2-1/3 hours. Light from a UV lamp was directed on the reaction mixture during the addition and the reaction mixture was refluxed for another hour. 25 Ml more of dry carbon tetrachloride was added and the refluxing was continued for about 16 hours more while UV radiation was applied. The reaction was then filtered through CELITE diatomaceous earth to remove the mercury salt. The carbon tetrachloride was removed on a still and the product was distilled over to yield 2.45 g of a yellow oil with analysis of, in percent by weight:

1. temperaturerefluxed 1 hour and 25 minutes
2. temperatureat reflux over the next 2-1/3 hours
3. additionLight from a UV lamp was directed on the reaction mixture during the addition
4. temperaturethe reaction mixture was refluxed for another hour
5. filtrationThe reaction was then filtered through CELITE diatomaceous earth
6. customto remove the mercury salt
7. customThe carbon tetrachloride was removed on a still and the product
8. distillationwas distilled over

ORD-Eintrag

ord-921dccb5e36f4adb9c8144fc408c0c56

Quelldatensatz

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04851539