Hydrochloric Acid → 4-(3-Chloro-1-phenyl-1-propenyl)(1,1'-biphenyl)

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Reaction Steps

A mixture of ((1,1′-biphenyl)-4-yl)phenylmethanone (0.01 mol) in THF (200 ml) was stirred at room temperature under N2 flow. Vinylmagnesium chloride (0.011 mol; 1M solution in THF) was added dropwise. The mixture was stirred at room temperature for 1 hour. HCl (150 ml) was added. The mixture was stirred at room temperature for 1 hour and extracted with DIPE. The organic layer was separated, washed once with a saturated K2CO3 solution, twice with H2O and once with a saturated NaCl solution, then dried, filtered and the solvent was evaporated. This fraction was purified by column chromatography over silica gel (eluent: CH2Cl2hexane/EtOAc 50/30/20). Two pure fractions were collected and their solvents were evaporated, yielding 8.8 g (29%) of 4-(3-chloro-1-phenyl-1-propenyl)(1,1′-biphenyl) (interm. 22).

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