Potassium Carbonate → 2,4'-dimethoxybiphenyl

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Reaction Steps

At 120° C., p-iodoanisole is reacted with 2-methoxyphenylboronic acid in the presence of palladium tetraphenyl phosphate, potassium carbonate and the phase transfer catalyst, tetrabutyl ammonium bromide to yield 2,4′-dimethoxybiphenyl (66%), which is then brominated at 0° C. in ethylene dichloride to produce 5,5′-dibromo-2,4′-dimethoxybiphenyl in 80% yield. n-butyl bromide is reacted with the dibromo intermediate in the presence of magnesium and cuprous iodide at −10° C. to produce in 50% yield 3′,5-dibutyl-2,4′-dimethoxy-1,1′-biphenyl. Demethylation with boron tribromide gives 3′,5-dibutyl-2,4′-dihydroxy-1,1′-biphenyl (17% yield).

Provenance & Evidence