Methane → HCID 67347233, compound

Temperature

95 °C

A mixture of 4-bromo-1-naphthalenecarboxylic acid (100 g), benzylacrylate (96.8 g), triphenylphosphine (10.2 g) palladium(II) acetate (2 g), triethylamine (258 ml) and DMF (600 ml) are heated at 90-100° C. for 4-12 h (typically 10-12 h). Two further portions of palladium(II) acetate (20 g) are added at four hour intervals during the stir period. The mixture is treated with charcoal (3×15 g) at 50-80° C. (typically 70-80° C.) filtering after each charge at 40-45° C. The DMF is then distilled off at 80-90° C. under vacuum and the residue is cooled to 25-35° C. Dichloromethane (100 ml) and water (100 ml) are added to the residue and the mixture is acidified with concentrated hydrochloric acid and is stirred at 20-35° C. for about 30 min. The mixture is filtered, and the solid product dried. The residue is dissolved in a mixture of DMF (600 ml) then water (400 ml) at 90-100° C. and stirred for 1-1.5 h. The solution is filtered at 80-85° C., cooled to 20-35° C., and stirred for about 2 h. The product is filtered off and dried (dry weight 43 g).

1. filtrationfiltering after
2. additioneach charge at 40-45° C
3. distillationThe DMF is then distilled off at 80-90° C. under vacuum
4. temperaturethe residue is cooled to 25-35° C
5. additionDichloromethane (100 ml) and water (100 ml) are added to the residue
6. filtrationThe mixture is filtered
7. customthe solid product dried
8. dissolutionThe residue is dissolved in a mixture of DMF (600 ml)
9. stirringwater (400 ml) at 90-100° C. and stirred for 1-1.5 h
10. filtrationThe solution is filtered at 80-85° C.
11. temperaturecooled to 20-35° C.
12. stirringstirred for about 2 h
13. filtrationThe product is filtered off
14. customdried
15. custom(dry weight 43 g)

ORD record

ord-ca3b0afaa72146a79c90ec4b874560e0

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989629B2