1-Bromo-4-tert-butylbenzene → 2-(4-t-butylphenyl)-2-methyl-5-(N-methyl-anilinomethylene)-cyclopentanone

Temperature

40 °C

An oven dried Schlenk tube equipped with a rubber septum was cooled under an argon urge. The septum was removed and the tube was charged with palladium acetate (5.6 mg, 0.025 mmol, 5 mol % Pd), (±)-BINAP (23.3 mg, 0.0375 mmol, 7.5 mol %) and 2-methyl-5-(N-methyl-anilinomethylene)-cyclopentanone (108 mg, 0.5 mmol). Toluene (2 mL) was added and the mixture was stirred for 1 min at 40° C. 4-t-Butylbromobenzene (0.17 mL, 1.0 mmol) and sodium t-butoxide (96 mg, 1.0 mmol) were added to the tube, the tube was capped with the septum, purged with argon, and additional toluene (4 mL) was added through the septum. The mixture was heated to 100° C. with stirring until the starting ketone had been completely consumed as judged by GC analysis. The mixture was cooled to room temperature, quenched with saturated aqueous ammonium chloride (10 mL) and diluted with ether (20 mL). The mixture was poured into a separatory funnel and the layers were separated. The aqueous layer was extracted with ether (20 mL), and the combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 116 mg (67%) of the title compound.

1. customAn oven dried Schlenk tube
2. customequipped with a rubber septum
3. temperaturewas cooled under an argon urge
4. customThe septum was removed
5. customthe tube was capped with the septum
6. custompurged with argon, and additional toluene (4 mL)
7. additionwas added through the septum
8. temperatureThe mixture was heated to 100° C.
9. stirringwith stirring until the starting ketone
10. customhad been completely consumed
11. temperatureThe mixture was cooled to room temperature
12. customquenched with saturated aqueous ammonium chloride (10 mL)
13. additiondiluted with ether (20 mL)
14. additionThe mixture was poured into a separatory funnel
15. customthe layers were separated
16. extractionThe aqueous layer was extracted with ether (20 mL)
17. washthe combined organic layers were washed with brine (20 mL)
18. dry with materialdried over anhydrous magnesium sulfate
19. filtrationfiltered
20. concentrationconcentrated in vacuo
21. customThe crude material was purified by flash chromatography on silica gel

ORD record

ord-1c3f66e370f146a9957c64c30c1a48fa

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06867310B1