Aluminium lithium hydride → [4'-(3-Fluoro-3-methylbutoxy)-2,2'-dimethylbiphenyl-3-yl]methanol

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Reaction Steps

In an atmosphere of nitrogen, a mixture of 1-bromo-4-(3-fluoro-3-methylbutoxy)-2-methylbenzene, methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, palladium acetate, dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, tripotassium phosphate, toluene and water was stirred at 80° C. for 12 hours to obtain methyl 4′-(3-fluoro-3-methylbutoxy)-2,2′-dimethylbiphenyl-3-carboxylate. Lithium aluminum hydride was added to a THF solution of the resulting methyl 4′-(3-fluoro-3-methylbutoxy)-2,2′-dimethylbiphenyl-3-carboxylate under ice-cooling, followed by warming up to room temperature and stirring for 1 hour to obtain [4′-(3-fluoro-3-methylbutoxy)-2,2′-dimethylbiphenyl-3-yl]methanol.

Provenance & Evidence