反应详情

A 5 L round bottom flask was equipped with mechanical stirring, a reflux condenser and ice bath. 488.2 g distilled 7-chloro-2-methylindene (2.97 mol) was added, dissolved in 2 L ether and 32.2 g Ni(dpp) (0.059 mol, 2 mol %) slurried in the solution, and stirred to cool to 0°-2° C. 1.05 L of 3.1M phenylmagnesium bromide in ether (3.25 mol, 10% excess) was added slowly from an addition funnel so that the temperature remained below 5° C. Once complete, the ice bath was removed, and the reaction stirred up to room temperature. The reaction was refluxed for 8 hours, and checked for completion by GC. The reaction flask was cooled with an ice bath, and 250 mL water added, then 1 L 10% HCl. The aqueous and organic layers are separated, and the organic layer dried over anhydrous Na2SO4. Ether was distilled, and the residual oil placed on a column of 100 g silica gel. Elution with hexane was performed, the hexane distilled under reduced pressure to a temperature of 90° C. 2-methyl-7-phenylindene (Spaleck compound 13a) was obtained by distillation at <1 mm Hg with a 36 cm Vigreux column at 125° C. A fore-cut containing biphenyl was obtained at 70°-90° C. and discarded. Yield was 507.8 g (2.47 mol) equal to 80%.

1. customA 5 L round bottom flask was equipped with mechanical stirring, a reflux condenser and ice bath
2. additionwas added
3. temperatureto cool to 0°-2° C
4. customremained below 5° C
5. customOnce complete, the ice bath was removed
6. stirringthe reaction stirred up to room temperature
7. temperatureThe reaction was refluxed for 8 hours
8. temperatureThe reaction flask was cooled with an ice bath
9. addition250 mL water added
10. customThe aqueous and organic layers are separated
11. dry with materialthe organic layer dried over anhydrous Na2SO4
12. distillationEther was distilled
13. washElution with hexane
14. distillationthe hexane distilled under reduced pressure to a temperature of 90° C