Triphenylphosphine → HCID 15781018, compound

Temperature

50 °C

After adding 2-bromo-4-fluorophenol (4.16 g, 20.32 mmol, Aldrich) into a flask, nitrogen flow is allowed into the flask. Then, palladium acetate (0.22 g, 1.02 mmol), potassium phosphate (21.00 g, 91.19 mmol), phenylboronic acid (2.97 g, 24.36 mmol), triphenylphosphine (0.80 g, 3.06 mmol) were added into the flask. Dimethoxyethane (32 ml) and distilled water (8 ml) were added thereto and stirred thoroughly. The mixture was heated to 50° C. and stirred for 6 hours. When the reaction is over, the mixture was allowed to cool at a room temperature, and then the organic layer was separated from the mixture by using diethylether (10 ml×3) and water. After adding magnesium sulfate to the separated organic layer, it was stirred for 30 minutes. The mixture was filtered and volatile materials of the mixture were then removed. The residue was added in a dried flask and dissolved in methylenechloride. After decreasing the temperature up to −78° C., boron tribromide (30.48 ml of 1.0M solution in methylenechloride, Aldrich) was slowly dropped thereon. When the dropped boron tribromide settled down, it was then allowed to react for 1 hour, and the temperature of the mixture was raised at a room temperature, and then stirred for 12 hours. An organic layer was separated from the obtained product by using diethylether (10 ml×3) and water, and then the organic layer was stirred for 30 minutes with added magnesium sulfate. After filtration, the volatile materials were removed, and then the resulting product was purified through a chromatography column packed with silica gel using hexane and methylchloride (1.5:1) as mobile phase. Then, after removing the volatiles, 3.76 g of white solid was obtained.

1. distillationDimethoxyethane (32 ml) and distilled water (8 ml)
2. additionwere added
3. stirringstirred for 6 hours
4. temperatureto cool at a room temperature
5. customthe organic layer was separated from the mixture
6. additionAfter adding magnesium sulfate to the separated organic layer, it
7. stirringwas stirred for 30 minutes
8. filtrationThe mixture was filtered
9. customvolatile materials of the mixture were then removed
10. additionThe residue was added in a dried flask
11. dissolutiondissolved in methylenechloride
12. customup to −78° C., boron tribromide (30.48 ml of 1.0M solution in methylenechloride, Aldrich)
13. additionwas slowly dropped
14. customto react for 1 hour
15. temperaturethe temperature of the mixture was raised at a room temperature
16. stirringstirred for 12 hours
17. customAn organic layer was separated from the obtained product
18. stirringthe organic layer was stirred for 30 minutes with added magnesium sulfate
19. filtrationAfter filtration
20. customthe volatile materials were removed
21. customthe resulting product was purified through a chromatography column
22. customThen, after removing the volatiles

ORD record

ord-0f2904b807a142eeb7b11f92b500dd7f

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589042B2