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

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Reaction Steps

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) is added to a solution of potassium t-butoxide (35 g; 0.31 mol) dissolved in DMSO (125 mL) dropwise slowly over a 1-hour period. After the addition, the mixture is further stirred for 4 hours at room temperature and then slowly poured into a stirred, ice-cold solution of ammonium chloride with vigorous stirring. The resulting tan precipitate is filtered, pressed, washed with methanol, and air-dried to give 20 g of the title compound as a pale yellow solid (67%): 1H nmr (400 MHz, CDCl3) d 2.30 (s, 6 H), 2.32 (s, 3 H), 5.76 (s, 1 H), 6.93 (s, 2 H), 7.12 (d, 1 H), 7.21 (dd, 1 H), 7.63 (t, 1 H), 8.63 (d, 1 H).

Provenance & Evidence