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0 °C

To a stirred solution of 4-(methylthio)benzonitrile (25.0 g, 0.17 mol) in THF (100 mL) under N2 atmosphere was added phenethylmagnesium chloride (1.0 M in THF, 210 mL, 0.21 mol). The solution was heated to reflux for 4 hours, cooled to 0° C., and quenched carefully with water (10 mL). The resulting slurry was treated with 6 N hydrochloric acid (200 mL) and stirred at room temperature overnight. The THF was evaporated from the mixture, and the residue was extracted with EtOAc (2×300 mL). The combined organic extracts were washed with 2M Na2CO3, dried over Na2SO4, filtered, and concentrated to give a solid material. Recrystallization from EtOAc-Hex (1:4) afforded the title compound (41.5 g, 96%) as greenish plates. mp 105° C. 1H NMR (300 MHz, CDCl3) δ 7.85 (d, J=8.5 Hz, 2H), 7.32–7.19 (m, 7H), 3.24 (t, J=6.8 Hz, 2H), 3.06 (t, J=6.8 Hz, 2H), 2.50 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 198.2, 145.8, 141.3, 133.2 128.48, 128.42, 128.38, 126.1, 125.0, 40.2, 30.2, 14.7; mass spectrum (API-TIS) m/z 257 (M+H).

1. temperatureThe solution was heated
2. temperatureto reflux for 4 hours
3. customquenched carefully with water (10 mL)
4. additionThe resulting slurry was treated with 6 N hydrochloric acid (200 mL)
5. customThe THF was evaporated from the mixture
6. extractionthe residue was extracted with EtOAc (2×300 mL)
7. washThe combined organic extracts were washed with 2M Na2CO3
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto give a solid material
12. customRecrystallization from EtOAc-Hex (1:4)