Synthesis
To a suspension of potassium flfluoride (350 mg, 6.0 mmol, spray dried) in DMF (50 mL) were added ethyldiflfluoro-(4-methyl)silane (560 mg, 3.0 mmol), 3-iodobenzyl alcohol (250 mg, 2.0 mmol), and (η3 -C3H5PdCl)2 (37 mg, 0.1 mmol). The resulting mixture was stirred at 100 °C for 15 h, cooled to room temperature, poured into saturated aqueous sodium bicarbonate solution, and extracted with diethyl ether (3 × 20 mL). The combined ethereal layer was then dried over magnesium sulfate. The solvent was removed under reduced pressure. The crude material was purifified by silica gel chromatography eluting a mixture of hexane:EtOAc (5:1) to give 340 mg (86%) of 3-hydroxymethyl-4´-methylbiphenyl as a colorless solid.Reference: Hatanaka, Y; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 50, 8301−8316.
