1-Bromo-2,6-difluorobenzene → HCID 22473553, compound

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Reaction Steps

2-Bromo-1,3-difluorobenzene (3.0 g, 15.5 mmol) was coupled to 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile (4.63 g, 20.2 mmol) as described in Example 51. The resulting black solid was purified by chromatography on silica gel eluting with isohexane on a gradient of ethyl acetate (10-15%). Trituration with isohexane (20 ml) gave 2′,6′-difluorobiphenyl-2-carbonitrile as a pale yellow solid (3.34 g, 100%): δH (360 MHz, CDCl3) 7.06 (2H, dd, J 8 and 7), 7.38-7.44 (1H, m), 7.47-7.56 (2H, m), 7.61-7.72 (1H, m), 7.82 (1H, dd, J 8 and 1).

Provenance & Evidence