Acetic Acid → HCID 59583113, compound

Temperature

0 °C

An oven-dried 500 mL, 3-neck flask with magnetic stirrer, addition funnel, thermocouple and nitrogen inlet was charged with anhydrous zinc chloride (15.0 g, 0.11 mol) and cooled in an ice/salt bath. 100 mL of THF was then added dropwise. Butyllithium (134 mL, 2.5 M in hexanes, 0.34 mol) was then added dropwise such that the temperature was maintained below 0° C., giving a milky white solution that was stirred at 0° C. for 30 minutes. The ice/salt bath was replaced with a dry ice/acetone bath and the reaction cooled to −75° C. N,N-bis(2,2-dibromovinyl)pyridin-2-amine (5.0 g, 0.011 mol) in 50 mL of THF was added dropwise and the reaction stirred at −75° C. for 20 h. While still at −75° C., 100 mL of 10% acetic acid in THF was added dropwise and the cold solution poured into 150 mL of 1 N HCl. The reaction mixture was extracted with 3×100 mL of ether and the combined organics were washed with 2×100 mL of saturated NaHCO3, dried and evaporated leaving 3.0 g of an colorless liquid as the product.

1. additionAn oven-dried 500 mL, 3-neck flask with magnetic stirrer, addition funnel
2. temperaturecooled in an ice/salt bath
3. temperaturewas maintained below 0° C.
4. customgiving a milky white solution that
5. temperaturethe reaction cooled to −75° C
6. stirringthe reaction stirred at −75° C. for 20 h
7. extractionThe reaction mixture was extracted with 3×100 mL of ether
8. washthe combined organics were washed with 2×100 mL of saturated NaHCO3
9. customdried
10. customevaporated

ORD record

ord-1aa1cf6087b942a793104060080b0d8e

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586203B2