4-Chlorotoluene → 4-Methylbiphenyl

An oven dried resealable Schlenk tube was purged with argon and charged with palladium acetate (4.4 mg, 0.02 mmol, 2 mol %), ligand 2 [Example 1] (11.9 mg, 0.03 mmol, 3 mol %), phenylboron dihydroxide (183 mg, 1.5 mmol), and cesium fluoride (456 mg, 3.0 mmol). The tube was purged with argon, and dioxane (3 mL) and 4-chlorotoluene (0.12 mL, 1.0 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 until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (20 mL) and poured into a separatory funnel. The mixture was washed with 1M NaOH (20 mL), and the layers were separated. The aqueous layer was extracted with ether (20 mL), and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was then purified by flash chromatography on silica gel to give 157 mg (93%) of a glassy solid.

1. customAn oven dried resealable Schlenk tube
2. customwas purged with argon
3. additionwere added through a rubber septum
4. customThe septum was removed
5. customthe tube was sealed with a teflon
6. customscrew cap
7. customhad been completely consumed
8. additionThe reaction mixture was then diluted with ether (20 mL)
9. additionpoured into a separatory funnel
10. washThe mixture was washed with 1M NaOH (20 mL)
11. customthe layers were separated
12. extractionThe aqueous layer was extracted with ether (20 mL)
13. dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
14. filtrationfiltered
15. concentrationconcentrated in vacuo
16. customThe crude material was then purified by flash chromatography on silica gel

ORD record

ord-a7e18cfdb83e4d6996b0398a3246b81a

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560582B2