Dimethylformamide → 2-(4-Bromo-2-trifluoromethyl-phenyl)2-methyl-propionitrile

Participants

Reaction Steps

NaH 95% (2.28 g, 94.7 mmol) was suspended in DMF (25mL) and cooled to 0° C. (4-Bromo-2-trifluoromethyl-phenyl)-acetonitrile (5 g, 18.94 mmol) from step 2 above, was dissolved in THF (35 mL) and slowly added via cannula to the NaH suspension. The reaction mixture was stirred for 20 min. Methyl iodide (11.79 mL, 189.36 mmol) was added and the resulting mixture was stirred overnight at room temperature. Reaction was quenched with H2O (100 mL). Solvents were removed in vacuo and residue partitioned between EtOAc and 1 N HCl (100 mL). The organic phase was dried over Na2SO4 and evaporated. The crude organic product was purified by flash column chromatography (5% EtOAc in hexanes) to give the product (4.14 g, 75%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 1.6 (s, 6H), 7.46 (d, J=5.3 Hz, 1 H), 7.67 (d, J=8.3 Hz, 1 H), 7.78 (s, 1H).

Provenance & Evidence