2-tert-butylsulfanylbenzonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(tert-butylthio)benzonitrile (Guiu, E. et al., J. Organomet. Chem., 689:1911-1918 (2004)) (1.00 g, 5.23 mmol) in THF (10.5 mL) was added BH3.THF (10.5 mL, 10.5 mmol, 1.0M solution in THF) via syringe. The resulting clear, colorless solution was stirred at room temperature for 1.5 h and then at 50° C. for 2 h. The reaction mixture was cooled to room temperature, and MeOH (2.5 mL) was added carefully via syringe (gas evolution) followed by 1N aq. HCl solution (12.0 mL). The mixture was poured into EtOAc and the layers were separated. The aqueous layer was basified with 1N aq. NaOH solution (pH=12) and then extracted with CH2Cl2 (5×). The combined CH2Cl2 extracts were dried over MgSO4, filtered and concentrated in vacuo to give the title compound (288 mg, 28%) as a colorless oil. 1H NMR (CDCl3) δ 7.57-7.53 (m, 1H), 7.44-7.40 (m, 1H), 7.37-7.32 (m, 1H), 7.25-7.19 (m, 1H), 4.07 (s, 2H), 1.30 (s, 9H); MS(ESI+) m/z 196.2 (M+H)+. at 50° C. for 2 h The reaction mixture was cooled to room temperature the layers were separated extracted with CH2Cl2 (5×) The combined CH2Cl2 extracts were dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(tert-butylthio)benzonitrile (Guiu, E. et al., J. Organomet. Chem., 689:1911-1918 (2004)) (1.00 g, 5.23 mmol) in THF (10.5 mL) was added BH3.THF (10.5 mL, 10.5 mmol, 1.0M solution in THF) via syringe. The resulting clear, colorless solution was stirred at room temperature for 1.5 h and then at 50° C. for 2 h. The reaction mixture was cooled to room temperature, and MeOH (2.5 mL) was added carefully via syringe (gas evolution) followed by 1N aq. HCl solution (12.0 mL). The mixture was poured into EtOAc and the layers were separated. The aqueous layer was basified with 1N aq. NaOH solution (pH=12) and then extracted with CH2Cl2 (5×). The combined CH2Cl2 extracts were dried over MgSO4, filtered and concentrated in vacuo to give the title compound (288 mg, 28%) as a colorless oil. 1H NMR (CDCl3) δ 7.57-7.53 (m, 1H), 7.44-7.40 (m, 1H), 7.37-7.32 (m, 1H), 7.25-7.19 (m, 1H), 4.07 (s, 2H), 1.30 (s, 9H); MS(ESI+) m/z 196.2 (M+H)+. at 50° C. for 2 h The reaction mixture was cooled to room temperature the layers were separated extracted with CH2Cl2 (5×) The combined CH2Cl2 extracts were dried over MgSO4 filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(tert-butylthio)benzonitrile (Guiu, E. et al., J. Organomet. Chem., 689:1911-1918 (2004)) (1.00 g, 5.23 mmol) in THF (10.5 mL) was added BH3.THF (10.5 mL, 10.5 mmol, 1.0M solution in THF) via syringe. The resulting clear, colorless solution was stirred at room temperature for 1.5 h and then at 50° C. for 2 h. The reaction mixture was cooled to room temperature, and MeOH (2.5 mL) was added carefully via syringe (gas evolution) followed by 1N aq. HCl solution (12.0 mL). The mixture was poured into EtOAc and the layers were separated. The aqueous layer was basified with 1N aq. NaOH solution (pH=12) and then extracted with CH2Cl2 (5×). The combined CH2Cl2 extracts were dried over MgSO4, filtered and concentrated in vacuo to give the title compound (288 mg, 28%) as a colorless oil. 1H NMR (CDCl3) δ 7.57-7.53 (m, 1H), 7.44-7.40 (m, 1H), 7.37-7.32 (m, 1H), 7.25-7.19 (m, 1H), 4.07 (s, 2H), 1.30 (s, 9H); MS(ESI+) m/z 196.2 (M+H)+. at 50° C. for 2 h The reaction mixture was cooled to room temperature the layers were separated extracted with CH2Cl2 (5×) The combined CH2Cl2 extracts were dried over MgSO4 filtered concentrated in vacuo