Dimethylformamide → HCID 86684913, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-Fluoro-3-trifluoromethyl-phenyl)-2-methyl-pyridine (51.0 g, ˜200 mmol) in THF (100 mL) were carefully added at room temperature 2-methyl-2-propanethiol (23.5 g, 260 mmol) and DMF (29.2 g, 400 mmol). Sodium-tert-butoxide solution 25% in THF (96.1 g=106 mL, 250 mmol, Chemetall) was added over 50 min and the beige suspension was stirred at 50° C. for 17 h. The brownish suspension was transferred into a separatory funnel, filled with TBME (500 mL), and washed with water (500 mL) and with 10% brine (500 mL). The two aqueous layers were extracted with TBME (300 mL) and the combined organic layers were dried (Na2SO4). Filtration and evaporation (45° C./≧10 mbar) afforded crude title product (65.5 g, 100.6%) as a brown oil which was used without purification in the next step. 1H NMR (CDCl3, 400 MHz) δ 1.39 (s, 9H), 2.65 (s, 3H), 7.33 (d, J=5.1 Hz, 1H), 7.39 (s, 1H), 7.73 (dd, J1=8.1 Hz, J2=1.9 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.96 (d, J=1.9, 1H), 8.60 (d, J=5.4, 1H). ESI-MS (m/z) [M+H]+326 (100).

Provenance & Evidence