4-Chlorotoluene → 4-Hexylanisole

General procedure for K3PO4 promoted Suzuki coupling of aryl chlorides: An oven-dried resealable Schlenk tube was purged with argon and charged with Pd(OAc)2 (0.01 mmol, 0.5 mol %), ligand 2 (0.015 mmol, 0.75 mol %), the boronic acid (3.0 mmol), and potassium phosphate (4.0 mmol). The tube was purged with argon, and dioxane (6 mL) and 4-chlorotoluene (2.0 mmol) were added through a rubber septum. The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at room temperature for 2 min, then heated to 100° C. with stirring until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then cooled to room temperature, diluted with ether (20 mL) and poured into a separatory funnel. The mixture was washed with 1 M NaOH (20 mL), and the layers were separated. The aqueous layer was extracted with ether (20 mL), and the combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was then purified by flash chromatography on silica gel.

1. customGeneral procedure for K3PO4 promoted Suzuki coupling of aryl chlorides: An oven-dried resealable Schlenk tube was purged with argon
2. additionwere added through a rubber septum
3. customThe septum was removed
4. customthe tube was sealed with a teflon
5. customscrew cap
6. temperatureheated to 100° C.
7. stirringwith stirring until the starting aryl chloride
8. customhad been completely consumed
9. temperatureThe reaction mixture was then cooled to room temperature
10. additiondiluted with ether (20 mL)
11. additionpoured into a separatory funnel
12. washThe mixture was washed with 1 M NaOH (20 mL)
13. customthe layers were separated
14. extractionThe aqueous layer was extracted with ether (20 mL)
15. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
16. filtrationfiltered
17. concentrationconcentrated in vacuo
18. customThe crude material was then purified by flash chromatography on silica gel

ORDレコード

ord-a382e65e648b4e1abb7ae64fad4aa7df

出典データセット

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07247731B2