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Ethyl 4-bromobenzoate undergoes reduction with potassium diisobutyl-t-butoxyaluminum hydride (PDBBA) at 0°C to yield aldehydes. Reaction of ethyl 4-bromobenzoate and substituted benzyl chloride with zinc dust and a Pd catalyst is reported.
Chae MJ, et al. Chemoselective Reduction of Esters to Aldehydes by Potassium Diisobutyl-t-butoxyaluminum Hydride (PDBBA). Bull. Korean Chem. Soc. 2007, 28 (12), 2517.
John M. Herbert. Negishi-type coupling of bromoarenes with dimethylzinc. Tetrahedron Letters. 2004, 45 (4), 817-819.
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