Hydrogen Bromide → 4-(Bromomethyl)pyridine hbr

Temperature

124 °C

4-Picolylacetate (300 g., 87% pure) was combined with 3.0 l. of 48% hydrobromic acid. A spontaneous exotherm occurred, the temperature rising from 26° to 42° C. The mixture was heated to reflux and refluxed for about 1 hour (pot temperature 124° C.). The reaction mixture was then concentrated in vacuo to yield a gummy solid which was dissolved in 1500 ml. of absolute alcohol. Crude hydrobromide salt (379 g.) crystallized on chilling and was recovered by filtration. Purified 4-picolylbromide hydrobromide (33.1 g., m.p. 187.5°-189° C.) was obtained by recrystallization of 50 g. of crude from absolute alcohol.

1. customrising from 26° to 42° C
2. temperatureThe mixture was heated
3. temperatureto reflux
4. concentrationThe reaction mixture was then concentrated in vacuo
5. customto yield a gummy solid which
6. dissolutionwas dissolved in 1500 ml
7. customCrude hydrobromide salt (379 g.) crystallized
8. temperatureon chilling
9. filtrationwas recovered by filtration

ORD record

ord-f414bb866b174f1994c33cabf314b6cf

Source dataset

uspto-grants-1981_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04246263