2,3,4,5,6-pentafluorobenzenethiol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of 4-acetoxybenzoyl chloride (4.96 g) in dry dichloromethane (20 ml) was added dropwise over 15 minutes to a stirred solution of pentafluorothiophenol (5.00 g), pyridine (2.1 ml) and 4-N,N-dimethylaminopyridine (50 mg) in dry dichloromethane (75 ml), the mixture being maintained close to 5° C. by immersion in an ice-bath. The reactants were allowed to reach room temperature overnight and the organic solution was washed successively with aqueous 2M hydrochloric acid, a saturated sodium bicarbonate solution and water. Evaporation of the solution, which had been dried over magnesium sulphate, afforded the desired thioester (8.79 g). the mixture being maintained close to 5° C. by immersion in an ice-bath the organic solution was washed successively with aqueous 2M hydrochloric acid Evaporation of the solution, which had been dried over magnesium sulphate

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

Procedure: A solution of 4-acetoxybenzoyl chloride (4.96 g) in dry dichloromethane (20 ml) was added dropwise over 15 minutes to a stirred solution of pentafluorothiophenol (5.00 g), pyridine (2.1 ml) and 4-N,N-dimethylaminopyridine (50 mg) in dry dichloromethane (75 ml), the mixture being maintained close to 5° C. by immersion in an ice-bath. The reactants were allowed to reach room temperature overnight and the organic solution was washed successively with aqueous 2M hydrochloric acid, a saturated sodium bicarbonate solution and water. Evaporation of the solution, which had been dried over magnesium sulphate, afforded the desired thioester (8.79 g). the mixture being maintained close to 5° C. by immersion in an ice-bath the organic solution was washed successively with aqueous 2M hydrochloric acid Evaporation of the solution, which had been dried over magnesium sulphate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Pentafluorothiophenol (5 g) was added to a solution of sodium hydroxide (2.0 g) in ethanol (50 ml) and the resulting solution was treated with a solution of 2-picolyl chloride, hydrochloride (4.1 g) in ethanol (25 ml). The mixture was stirred at ambient temperature for 4 hours, filtered through Kieselghur and the solvent removed by evaporation. The residue was converted into the hydrochloride with ethereal HCl solution and this was recrystallised from acetone-ether to give 2-(((pentafluorophenyl)thio)methyl)pyridine, hydrochloride (5.0 g) mp 157°-8° C. (Found: C,44.0; H,2.4; N,4.0; C12H6F5NS.HCl requires C,44.0; H,2.15; N,4.3%). filtered through Kieselghur the solvent removed by evaporation this was recrystallised from acetone-ether

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

Procedure: Pentafluorothiophenol (5 g) was added to a solution of sodium hydroxide (2.0 g) in ethanol (50 ml) and the resulting solution was treated with a solution of 2-picolyl chloride, hydrochloride (4.1 g) in ethanol (25 ml). The mixture was stirred at ambient temperature for 4 hours, filtered through Kieselghur and the solvent removed by evaporation. The residue was converted into the hydrochloride with ethereal HCl solution and this was recrystallised from acetone-ether to give 2-(((pentafluorophenyl)thio)methyl)pyridine, hydrochloride (5.0 g) mp 157°-8° C. (Found: C,44.0; H,2.4; N,4.0; C12H6F5NS.HCl requires C,44.0; H,2.15; N,4.3%). filtered through Kieselghur the solvent removed by evaporation this was recrystallised from acetone-ether

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

Procedure: Pentafluorothiophenol (5 g) was added to a solution of sodium hydroxide (2.0 g) in ethanol (50 ml) and the resulting solution was treated with a solution of 2-picolyl chloride, hydrochloride (4.1 g) in ethanol (25 ml). The mixture was stirred at ambient temperature for 4 hours, filtered through Kieselghur and the solvent removed by evaporation. The residue was converted into the hydrochloride with ethereal HCl solution and this was recrystallised from acetone-ether to give 2-(((pentafluorophenyl)thio)methyl)pyridine, hydrochloride (5.0 g) mp 157°-8° C. (Found: C,44.0; H,2.4; N,4.0; C12H6F5NS.HCl requires C,44.0; H,2.15; N,4.3%). filtered through Kieselghur the solvent removed by evaporation this was recrystallised from acetone-ether

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

Procedure: To a solution of 4-methoxybenzylbromide (2.00 g, 9.95 mmol) in DMF (20 ml) at room temperature was added potassium carbonate (2.07 g, 15.0 mmol) followed by pentafluorothiophenol (1.33 ml, 9.97 mmol). After stirring at room temperature for 1 h, the reaction mixture was poured onto water and extracted with diethyl ether. The combined organic extracts were washed with 1 M NaOH, dried and concentrated to give a white solid which was used directly in the next step. The sulfide (1.11 g, 3.47 mmol) was dissolved in dichloromethane (20 ml) and cooled to 0° C. m-chloroperbenzoic acid, MCPBA, (1.20 g, 6.95 mmol) was added and the resulting mixture stirred at room temperature for 2 h The reaction mixture was poured onto 1 M NaOH (50 ml) and extracted with dichloromethane (3×25 ml). The combined organic extracts were washed with brine, dried (MgSO4),concentrated and flash chromatographed (25:25:1, 20:20:3/hexanes:dichloromethane:ethyl acetate) to provide 413 mg (34%) of the title compound as a white solid. 1H NMR (CDCl3): d 7.18-7.22 (2H, m), 6.85-6.80 (2H, m), 4.48 (2H, s), 3.78 (3H, s). MS (EI): m/z 352 (2, M+), 121 (100). Anal. Calcd for C14H9F5O3S: C, 47.73; H, 2.58; S, 9.10. Found: C, 47.88; H, 2.66; S, 8.97. the reaction mixture was poured onto water extracted with diethyl ether The combined organic extracts were washed with 1 M NaOH dried concentrated to give a white solid which was added the resulting mixture stirred at room temperature for 2 h The reaction mixture extracted with dichloromethane (3×25 ml) The combined organic extracts were washed with brine, dried (MgSO4),concentrated and flash chromatographed (25:25:1, 20:20:3/hexanes:dichloromethane:ethyl acetate)

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

Procedure: To a solution of 4-methoxybenzylbromide (2.00 g, 9.95 mmol) in DMF (20 ml) at room temperature was added potassium carbonate (2.07 g, 15.0 mmol) followed by pentafluorothiophenol (1.33 ml, 9.97 mmol). After stirring at room temperature for 1 h, the reaction mixture was poured onto water and extracted with diethyl ether. The combined organic extracts were washed with 1 M NaOH, dried and concentrated to give a white solid which was used directly in the next step. The sulfide (1.11 g, 3.47 mmol) was dissolved in dichloromethane (20 ml) and cooled to 0° C. m-chloroperbenzoic acid, MCPBA, (1.20 g, 6.95 mmol) was added and the resulting mixture stirred at room temperature for 2 h. The reaction mixture was poured onto 1 M NaOH (50 ml) and extracted with dichloromethane (3×25 ml). The combined organic extracts were washed with brine, dried (MgSO4),concentrated and flash chromatographed (25:25:1, 20:20:3/hexanes:dichloromethane:ethyl acetate) to provide 413 mg (34%) of the title compound as a white solid. 1H NMR (CDCl3): d 7.18-7.22 (2H, m), 6.85-6.80 (2H, m), 4.48 (2H, s), 3.78 (3H, s). MS (EI): m/z 352 (2, M+), 121 (100). Anal Calcd. for C14H9F5O3S: C, 47.73; H, 2.58; S, 9.10. Found: C, 47.88; H, 2.66; S, 8.97. the reaction mixture was poured onto water extracted with diethyl ether The combined organic extracts were washed with 1 M NaOH dried concentrated to give a white solid which was added the resulting mixture stirred at room temperature for 2 h extracted with dichloromethane (3×25 ml) The combined organic extracts were washed with brine, dried (MgSO4),concentrated and flash chromatographed (25:25:1, 20:20:3/hexanes:dichloromethane:ethyl acetate)

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

Procedure: A solution of 4-acetoxybenzoyl chloride (4.96 g) in dry dichloromethane (20 ml) was added dropwise over 15 minutes to a stirred solution of pentafluorothiophenol (5.00 g), pyridine (2.1 ml) and 4-N,N-dimethylaminopyridine (50 mg) in dry dichloromethane (75 ml), the mixture being maintained close to 5° C. by immersion in an ice-bath. The reactants were allowed to reach room temperature overnight and the organic solution was washed successively with aqueous 2M hydrochloric acid, a saturated sodium bicarbonate solution and water. Evaporation of the solution, which had been dried over magnesium sulphate, afforded the desired thioester (8.79 g). the mixture being maintained close to 5° C. by immersion in an ice-bath the organic solution was washed successively with aqueous 2M hydrochloric acid Evaporation of the solution, which had been dried over magnesium sulphate