Nitrogen → HCID 19738077, compound

Participants

Reaction Steps

A solution of p-tolyltrimethyltin (1.26 g; 4.96 mmol) in dry toluene (8 mL) was degassed with a stream of N2 for ca. 5 min. To this solution under N2 was added 2-bromo-5-fluoro-benzonitrile (0.901 g; 4.51 mmol) and Pd(PPh3)4 (260 mg; 5 mol %). The reaction was stirred at reflux under N2 for 12 hr and then cooled to room temperature. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo. The product was purified by flash chromatography on a silica column eluting with Hex/CH2Cl2 to afford 0.606 g (64%) of the title compound as a slightly yellow solid. 1H-NMR (300 MHz, CDCl3) δ 2.40 (s, 3H), 7.28 (d, 2H), 7.34 (dd, 1H), 7.40 (d, 2H), 7.44 (t, 1H), 7.46 (dd, 1H); FAB mass spectrum, m/e 211 (m+, calcd for C14H10NF, 211).

Provenance & Evidence