Triphenylphosphine → HCID 15781018, compound

Temperature

50 °C

2-bromo-4-fluorophenol (4.16 g, 20.32 mmol, Aldrich) was added into the flask, and then nitrogen was introduced thereto. Palladium acetate (0.22 g, 1.02 mmol), potassium phosphate (21.00 g, 91.19 mmol), phenylboronic acid (2.97 g, 24.36 mmol) and triphenylphosphine (0.80 g, 3.06 mmol) were additionally added into the flask. DME (32 ml) and distilled water (8 ml) were added into, followed by stirring well. The mixture was heated to 50° C. and then stirred for 6 hours. After completion of the reaction, the reaction product was cooled to room temperature, and the organic layer was separated with ammonium chloride diethylether (10 ml×3) and distilled water. Then, magnesium sulfate was added to the collected organic layer, followed by stirring for 30 minutes. The mixture was filtered and treated to remove volatile material, thus obtained material was cooled to −78° C. followed by slowly adding borontribromide (30.48 ml, 1.0M in methylene chloride Aldrich) dropwise. After completion of the addition, the mixture was maintained at that temperature for 1 hour, and then warmed to room temperature and stirred for 12 hours. Then, the organic layer was separated with ammonium chloride diethylether (10 ml×3) and distilled water from the obtained material. Subsequently, magnesium sulfate was added to the collected organic layer, followed by stirring for 30 minutes. After filtering, removing volatile components, and the residue was passed through a silica gel chromatography column using a mixed solvent of hexane and methylene chloride (1.5:1) as moving phase. From obtained mixture, volatile components were removed to yield 3.76 g of 2-phenyl-4-fluorophenol as white solid.

1. additionnitrogen was introduced
2. distillationDME (32 ml) and distilled water (8 ml)
3. additionwere added into,
4. stirringstirred for 6 hours
5. customAfter completion of the reaction
6. temperaturethe reaction product was cooled to room temperature
7. customthe organic layer was separated with ammonium chloride diethylether (10 ml×3)
8. distillationdistilled water
9. additionThen, magnesium sulfate was added to the collected organic layer
10. stirringby stirring for 30 minutes
11. filtrationThe mixture was filtered
12. additiontreated
13. customto remove volatile material, thus obtained material
14. temperaturewas cooled to −78° C.
15. additionby slowly adding borontribromide (30.48 ml, 1.0M in methylene chloride Aldrich) dropwise
16. additionAfter completion of the addition
17. temperaturethe mixture was maintained at that temperature for 1 hour
18. temperaturewarmed to room temperature
19. stirringstirred for 12 hours
20. customThen, the organic layer was separated with ammonium chloride diethylether (10 ml×3)
21. distillationdistilled water from the obtained material
22. additionSubsequently, magnesium sulfate was added to the collected organic layer
23. stirringby stirring for 30 minutes
24. filtrationAfter filtering
25. customremoving volatile components
26. customFrom obtained mixture, volatile components
27. customwere removed

ORD record

ord-0a2b2ba89a4b47e0a8130640ba393a44

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07645715B2