52% |
With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere; |
5-fluoro-2-(methylsulfanyl)benzaldehyde
n-BuLi in hexane (2.5 M, 0.4 mL, 1 mmol) was added dropwise to a solution of 2-bromo- 4-fluoro-1-(methylsulfanyl)benzene (221.0 mg, 1 mmol) in dry THF (10 mL) at -78 °C under N2(g), so the temperature was maintained below -70 °C. DMF (80.0 mg, 1.1 mmol) was added and the reaction stirred at -78°C for a further 30 mins. The resulting mixture was quenched by the addition of ice-cold sat. aq. NH4CI soln. (10 mL), warmed to rt and extracted with EtOAc (10 mL). The organic extracts were washed with saturated brine (10 mL), dried (MgS0 ), concentrated in vacuo and purified by column chromatography on silica gel eluting with heptanes: EtOAc (95:5) to afford the title compound as colourless oil, 88 mg, 52%. 1 H NMR (CDCIs, 400MHz): d_2.51 (s, 3H), 7.25-7.30 (m, 1 H), 7.35-7.39 (m, 1 H), 7.52- 7.56 (m, 1 H), 10.35 (s, 1 H). |
52% |
With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere; |
5-Fluoro-2-(methylsulfanyl)benzaldehyde
n-BuLi in hexane (2.5 M, 0.4 ml, 1 mmol) was added dropwise to a solution of 2-bromo- 4-fluoro-1-(methylsulfanyl)benzene (221.0 mg, 1 mmol) in dry THF (10 ml) at -78°C under N2 atmosphere, so the temperature was maintained below -70°C. DMF (80.0 mg, 1.1 mmol) was added and the reaction stirred at -78°C for a further 30 mins. The resulting mixture was quenched by the addition of ice-cold sat. aq. NH4CI solution (10 ml), warmed to rt and extracted with EtOAc (10 ml). The organic extracts were washed with saturated brine (10 ml), dried (MgS04), concentrated in vacuo and purified by column chromatography on silica gel eluting with heptanes: EtOAc (95:5) to afford the title compound as colourless oil (88 mg, 52%). 1 H NMR (CDCIs, 400MHz): d: 10.35 (s, 1 H); 7.52-7.56 (m, 1 H); 7.35-7.39 (m, 1 H), 7.25- 7.30 (m, 1 H); 2.51 (s, 3H). |
52% |
With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere; |
7 5-fluoro-2-(methylsulfanyl)benzaldehyde
n-BuLi in hexane (2.5 M, 0.4 ml_, 1 mmol) was added dropwise to a solution of 2-bromo- 4-fluoro-1-(methylsulfanyl)benzene (221.0 mg, 1 mmol) in dry THF (10 mL) at -78 °C under N2(g), so the temperature was maintained below -70 °C. DMF (80.0 mg, 1.1 mmol) was added and the reaction stirred at -78°C for a further 30 mins. The resulting mixture was quenched by the addition of ice-cold sat. aq. NH CI soln. (10 ml_), warmed to rt and extracted with EtOAc (10 ml_). The organic extracts were washed with saturated brine (10 ml_), dried (MgS04), concentrated in vacuo and purified by column chromatography on silica gel eluting with heptanes:EtOAc (95:5) to afford the title compound as colourless oil, 88 mg, 52%. 1H NMR (CDC , 400MHz): d_2.51 (s, 3H), 7.25-7.30 (m, 1H), 7.35-7.39 (m, 1H), 7.52- 7.56 (m, 1 H), 10.35 (s, 1 H). |