Catecholborane → trans-3-Methyl-3-(4-trifluoromethylphenyl)-1-butenylboronic acid

Temperature

70 °C

Under a nitrogen atmosphere, a stirred mixture of 25.2 grams (0.12 mole) of 3-methyl-3-(4-trifluoromethylphenyl)-1-butyne and 12.7 mL (0.12 mole) of 1,3,2-benzodioxaborole was warmed to 70° C. where it stirred for six hours. The reaction mixture was then cooled and poured slowly into 500 mL of ice-water while flushing with nitrogen. The mixture was then allowed to warm to ambient temperature where it stirred for about 18 hours. The mixture was cooled in an ice-bath, and the resultant solid was collected by filtration. The solid was washed with water and then dissolved in diethyl ether. The solution was washed with 100 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure to a residual solid. The solid was added under vacuum without heat, yielding 27.6 grams of trans-3-methyl-3-(4-trifluoromethylphenyl)-1-butenylboronic acid.

1. temperatureThe reaction mixture was then cooled
2. customwhile flushing with nitrogen
3. temperatureto warm to ambient temperature where it
4. stirringstirred for about 18 hours
5. temperatureThe mixture was cooled in an ice-bath
6. filtrationthe resultant solid was collected by filtration
7. washThe solid was washed with water
8. dissolutiondissolved in diethyl ether
9. washThe solution was washed with 100 mL of an aqueous solution saturated with sodium chloride
10. dry with materialThe organic layer was dried with magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure to a residual solid
13. additionThe solid was added under vacuum
14. temperaturewithout heat

ORD record

ord-6a7c54c4006142cf901db79431090812

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05622954