2,4,6-Trimethylpyridine → HCID 54049138, compound

Temperature

-60 °C

To a solution of 9.8 g of 4-cyanophenylethyl cyclopropyl carbinol in 140 ml of ether was added 4.24 g of lithium bromide and 3 ml of 2,4,6-collidine. The mixture was cooled to -60° C. and 9.8 g of phosphorus tribromide was added over a five minute period. The reaction mixture was allowed to warm to 0° C., kept at that temperature for two hours and then allowed to warm to 18° C. Collidine (18 ml) was added, and after 15 minutes of stirring, the mixture was poured into 200 ml of water and 100 ml of ether. The ether extracts were washed with dilute aqueous sulfuric acid and water, dried over anhydrous magnesium sulfate and concentrated to a volume of 150 ml. Zinc bromide (11.6 g) was then added with cooling, and the mixture was stirred at room temperature for 29 hours. The ether solution was washed with water, dried and concentrated to give 12.5 g of 4 -(6-bromohex-3-enyl)benzonitrile as a yellow oil.

1. temperatureto warm to 0° C.
2. temperatureto warm to 18° C
3. washThe ether extracts were washed with dilute aqueous sulfuric acid and water
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated to a volume of 150 ml
6. additionZinc bromide (11.6 g) was then added
7. temperaturewith cooling
8. stirringthe mixture was stirred at room temperature for 29 hours
9. washThe ether solution was washed with water
10. customdried
11. concentrationconcentrated

ORD record

ord-cbbb6767540b43d1945b4d6441d60bf0

Source dataset

uspto-grants-1984_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04451476