4-溴-3-氯苯-1-硫醇

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-Bromo-3-chloro-benzenethiol (0.94 g, 4.21 mmol) was dissolved in tetrahydrofuran (10 ml) and cooled to 0° C. under argon. Sodium hydride (0.19 g, 4.63 mmol) was added and the mixture was stirred for 5 minutes, then iodomethane (0.28 ml, 4.42 mmol) was added. The mixture was allowed to warm, stirring for 30 minutes, then the reaction was quenched with saturated aqueous ammonium chloride. The mixture was extracted with dichloromethane (×2) and the combined organic layers were dried (MgSO4) and concentrated. Purification of the resultant residue by flash chromatography (Si-PCC, pentane) afforded the title compound as a colourless oil (0.65 g, 65%). 1H NMR (CDCl3 400 MHz) 2.47 (3H, s), 6.99 (1H, dd, J=8.45, 2.26 Hz), 7.30 (1H, d, J=2.25 Hz), 7.48 (1H, d, J=8.45 Hz). to warm stirring for 30 minutes the reaction was quenched with saturated aqueous ammonium chloride The mixture was extracted with dichloromethane (×2) the combined organic layers were dried (MgSO4) concentrated Purification of the resultant residue by flash chromatography (Si-PCC, pentane)

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-Bromo-3-chloro-benzenesulfonyl chloride (3.78 g, 13.0 mmol) was dissolved in dichloromethane (40 ml) and DMF (1.0 ml) was added. The mixture was cooled to 0° C. under argon and triphenylphosphine (10.26 g, 39.0 mmol) was added slowly, then the mixture was allowed to return to room temperature with stirring over 16 h. Hydrochloric acid (1 M, 75 ml) was added and the layers were separated. The organic layer was concentrated and the residue suspended in 1 M aqueous sodium hydroxide (75 ml) and filtered. The filtrate was extracted with Et2O (×2), then neutralised (1 M HCl, 75 ml). The mixture was then extracted (Et2O×3) and the combined organic layers were dried (Na2SO4) and concentrated to afford the title compound as a colourless oil (0.94 g, 32%). 1H NMR (CDCl3 400 MHz) 3.49 (1H, s), 7.02 (1H, dd, J=8.35, 2.24 Hz), 7.38 (1H, d, J=2.18 Hz), 7.45 (1H, d, J=8.35 Hz). to return to room temperature the layers were separated The organic layer was concentrated filtered The filtrate was extracted with Et2O (×2) The mixture was then extracted (Et2O×3) the combined organic layers were dried (Na2SO4) concentrated

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-Bromo-3-chloro-benzenesulfonyl chloride (3.78 g, 13.0 mmol) was dissolved in dichloromethane (40 ml) and DMF (1.0 ml) was added. The mixture was cooled to 0° C. under argon and triphenylphosphine (10.26 g, 39.0 mmol) was added slowly, then the mixture was allowed to return to room temperature with stirring over 16 h. Hydrochloric acid (1 M, 75 ml) was added and the layers were separated. The organic layer was concentrated and the residue suspended in 1 M aqueous sodium hydroxide (75 ml) and filtered. The filtrate was extracted with Et2O (×2), then neutralised (1 M HCl, 75 ml). The mixture was then extracted (Et2O×3) and the combined organic layers were dried (Na2SO4) and concentrated to afford the title compound as a colourless oil (0.94 g, 32%). 1H NMR (CDCl3 400 MHz) 3.49 (1H, s), 7.02 (1H, dd, J=8.35, 2.24 Hz), 7.38 (1H, d, J=2.18 Hz), 7.45 (1H, d, J=8.35 Hz). to return to room temperature the layers were separated The organic layer was concentrated filtered The filtrate was extracted with Et2O (×2) The mixture was then extracted (Et2O×3) the combined organic layers were dried (Na2SO4) concentrated

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-Bromo-3-chloro-benzenesulfonyl chloride (3.78 g, 13.0 mmol) was dissolved in dichloromethane (40 ml) and DMF (1.0 ml) was added. The mixture was cooled to 0° C. under argon and triphenylphosphine (10.26 g, 39.0 mmol) was added slowly, then the mixture was allowed to return to room temperature with stirring over 16 h. Hydrochloric acid (1 M, 75 ml) was added and the layers were separated. The organic layer was concentrated and the residue suspended in 1 M aqueous sodium hydroxide (75 ml) and filtered. The filtrate was extracted with Et2O (×2), then neutralised (1 M HCl, 75 ml). The mixture was then extracted (Et2O×3) and the combined organic layers were dried (Na2SO4) and concentrated to afford the title compound as a colourless oil (0.94 g, 32%). 1H NMR (CDCl3 400 MHz) 3.49 (1H, s), 7.02 (1H, dd, J=8.35, 2.24 Hz), 7.38 (1H, d, J=2.18 Hz), 7.45 (1H, d, J=8.35 Hz). to return to room temperature the layers were separated The organic layer was concentrated filtered The filtrate was extracted with Et2O (×2) The mixture was then extracted (Et2O×3) the combined organic layers were dried (Na2SO4) concentrated