2-Bromopyridine → 2-(2-Pyridinyl)-2-(2,4,6-trimethylphenyl)ethanenitrile

Participants

Reaction Steps

Add dropwise over a 1-hour period a mixed solution of 2-(2,4,6-trimethylphenyl)ethanenitrile (20 g; 0.126 mol) and 2-bromopyridine (35 g; 0.22 mol) in DMSO (25 mL) to a solution of potassium t-butoxide (35 g; 0.31 mol) dissolved in DMSO (125 mL). After the addition, stir the mixture for 4 h at ambient temperature and slowly pour into a stirred, ice-cold solution of NH4Cl with vigorous stirring. Filter the resulting tan precipitate, wash with MeOH, and air-dry to obtain the title compound as a pale yellow solid: 1H NMR (400 MHz, CDCl3) δ 2.30 (s, 6H), 2.32 (s, 3H), 5.76 (s, 1H), 6.93 (s, 2H), 7.12 (d, 1H), 7.21 (dd, 1H), 7.63 (t, 1H), 8.63 (d, 1H).

Provenance & Evidence