Potassium Carbonate → 3'-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-fluoro-3-biphenylcarbonitrile

Participants

Reaction Conditions

Reaction Steps

3-Bromo-5-fluorobenzonitrile (5.00 g, 25.0 mmol), Pd(OAc)2 (0.15 g), PPh3 (0.60 g) and K2CO3 (5.18 g, 37.5 mmol) were dissolved in dioxane (60 mL). The mixture was heated at 70° C. for 30 min, then [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (7.99 g, 30.0 mmol) was added. The mixture reaction was stirred at reflux overnight. The solvent was removed under reduced pressure, then diluted with CH2Cl2 (100 mL). The organic layer was washed with water (50 mL) and brine (50 mL). And the organic layer was dried over Na2SO4. The product 3′-({[(1,1-dimethylethyl) (dimethyl)silyl]oxy}methyl)-5-fluoro-3-biphenylcarbonitrile (5.10 g, 60%) was purified by flash column chromatography. 1H NMR (400 MHz, CDCl3): δ 7.67 (t, J=5.2 Hz, 1 H), 7.54-7.32 (m, 5 H), 4.81 (s, 2 H), 0.94 (s, 9 H), 0.13 (s, 6 H).

Provenance & Evidence