Diethyl Ether → Stannane, trimethyl(4-methylphenyl)-

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Reaction Steps

41.4L of 1.0 M p-tolylmagnesium bromide in diethyl ether (41.4 mol) was added dropwise, maintaining the temperature below -5° C., over 4 hours to a solution of 546 g (2.79 mol) of trimethyltin chloride in tetrahydrofuran (4L) under nitrogen at -10 C. The suspension was allowed to warm slowly to room temperature over 12 h then saturated ammonium chloride solution (1L) was added followed by sufficient water (approximately 1L) to dissolve the precipitate. The solution was extracted with ether-hexane (1:1) (1×4L, 3×2L). The combined organic phases were washed with brine, dried over magnesium sulfate and the solvents removed under vacuum. Purification by flash chromatography on silica gel eluting with hexane/ethyl acetate (95:5) gave a pale yellow oil containing white crystals of 4,4'-dimethylbiphenyl which were removed by filtration to leave 711.3 g (100%) of product. 1H NMR (300MHz,CDCl3): 0.30 (s,9H), 2.34 (s,3 H), 7.19 (d,7.7Hz,2H), 7.40 (d,7.7Hz,2H).

Provenance & Evidence