Benzene, 1,1'-sulfonylbis[4-fluoro-

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

Procedure: 5 mmol of sodium 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanolate and 10 mmol of bis(4-fluorophenyl) sulphone are treated as described in Example 61 (method A).

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

Procedure: A 194 g (1.1 moles) quantity of 4-fluorobenzenesulfonic acid was added to 96 g (1 mole) of fluorobenzene and the mixture was cooled with water while 123 g (1.1 moles) of chlorosulfonic acid was added at about 10° to about 20° C. over a period of 1 hour. After the addition, the reaction mixture was stirred for 3 hours while being maintained at 20° to 30° C. The hydrochloric acid gas evolved during the reaction was continuously removed from the reaction system. After the completion of the reaction, about 400 ml of water was added to the reaction mixture, and 9.6 g (0.1 mole) of the unreacted fluorobenzene was recovered by distillation. Separation of the precipitate by filtration gave 65 g of 4,4'-difluorodiphenylsulfone in 58% yield. M.P. 97° to 98° C. Purity of 99.7%. was added at about 10° to about 20° C. over a period of 1 hour After the addition while being maintained at 20° to 30° C was continuously removed from the reaction system After the completion of the reaction, about 400 ml of water was recovered by distillation Separation of the precipitate by filtration

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (427 mg; 2.13 mmol), bis(4-fluorophenyl) sulfone (493 mg; 1.94 mmol) and potassium carbonate (1.01 g; 7.76 mmol) in dimethylsulfoxide (5 mL) is heated over night at 100° C. The temperature is then increased to 120° C. and the mixture is reacted at this temperature for 24 hours. The reaction is then diluted with dichloromethane (100 mL), filtered and the filtrate is washed with aq. 1N hydrochloric acid (2×20 mL), and water (2×20 mL). The organic layer is dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue obtained is finally purified by column chromatography on silica gel (dichloromethane:methanol 100:0 (200 mL) and then 98:2 (150 mL)) to afford the desired product (653 mg; 1.50 mmol). the mixture is reacted at this temperature for 24 hours filtered the filtrate is washed with aq. 1N hydrochloric acid (2×20 mL), and water (2×20 mL) The organic layer is dried over magnesium sulfate filtered concentrated under reduced pressure The residue obtained is finally purified by column chromatography on silica gel (dichloromethane:methanol 100:0 (200 mL)

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (427 mg; 2.13 mmol), bis(4-fluorophenyl) sulfone (493 mg; 1.94 mmol) and potassium carbonate (1.01 g; 7.76 mmol) in dimethylsulfoxide (5 mL) is heated over night at 100° C. The temperature is then increased to 120° C. and the mixture is reacted at this temperature for 24 hours. The reaction is then diluted with dichloromethane (100 mL), filtered and the filtrate is washed with aq. 1N hydrochloric acid (2×20 mL), and water (2×20 mL). The organic layer is dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue obtained is finally purified by column chromatography on silica gel (dichloromethane:methanol 100:0 (200 mL) and then 98:2 (150 mL)) to afford the desired product (653 mg; 1.50 mmol). the mixture is reacted at this temperature for 24 hours filtered the filtrate is washed with aq. 1N hydrochloric acid (2×20 mL), and water (2×20 mL) The organic layer is dried over magnesium sulfate filtered concentrated under reduced pressure The residue obtained is finally purified by column chromatography on silica gel (dichloromethane:methanol 100:0 (200 mL)

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

Procedure: Bis-(4-fluorophenyl) sulphone (100 g; 0.394 mole), potassium hydroxide solution (91.98 g; 0.787 mole KOH) and dimethyl sulphoxide (400 cm3) were stirred together in a stainless steel vessel under nitrogen at 57° C. for 24 hours. Two liquid phases remained throughout the reaction. The reaction mixture was diluted with water and twice extracted with diethyl ether to recover non-phenolic material (9 g). The aqueous phase was then acidified and the phenolic component (86 g; m.p. 150°-154° C.) was extracted with more ether. By subliming this product under a diffusion pump at 180° C., followed by recrystallisation from toluene (400 cm3), 4-(4-fluorophenylsulphonyl)phenol (72.5 g) was obtained, m.p. 158°-159° C. The potassium salt was obtained from this phenol as a very pale yellow solid. Two liquid phases remained throughout the reaction twice extracted with diethyl ether to recover non-phenolic material (9 g) the phenolic component (86 g; m.p. 150°-154° C.) was extracted with more ether at 180° C. followed by recrystallisation from toluene (400 cm3)

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

Procedure: Bis-(4-fluorophenyl) sulphone (100 g; 0.394 mole), potassium hydroxide solution (91.98 g; 0.787 mole KOH) and dimethyl sulphoxide (400 cm3) were stirred together in a stainless steel vessel under nitrogen at 57° C. for 24 hours. Two liquid phases remained throughout the reaction. The reaction mixture was diluted with water and twice extracted with diethyl ether to recover non-phenolic material (9 g). The aqueous phase was then acidified and the phenolic component (86 g; m.p. 150°-154° C.) was extracted with more ether. By subliming this product under a diffusion pump at 180° C., followed by recrystallisation from toluene (400 cm3), 4-(4-fluorophenylsulphonyl)phenol (72.5 g) was obtained, m.p. 158°-159° C. The potassium salt was obtained from this phenol as a very pale yellow solid. Two liquid phases remained throughout the reaction twice extracted with diethyl ether to recover non-phenolic material (9 g) the phenolic component (86 g; m.p. 150°-154° C.) was extracted with more ether at 180° C. followed by recrystallisation from toluene (400 cm3)

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

Procedure: Bis-(4-fluorophenyl) sulphone (100 g; 0.394 mole), potassium hydroxide solution (91.98 g; 0.787 mole KOH) and dimethyl sulphoxide (400 cm3) were stirred together in a stainless steel vessel under nitrogen at 57° C for 24 hours. Two liquid phases remained throughout the reaction. The reaction mixture was diluted with water and twice extracted with diethyl ether to recover non-phenolic material (9 g). The aqueous phase was then acidified and the phenolic component (86 g; m.p. 150°-154° C) was extracted with more ether. By subliming this product under a diffusion pump at 180° C, followed by recrystallisation from toluene (400 cm3), 4-(4-fluorophenylsulphonyl)phenol (72.5 g) was obtained, m.p. 158°-159° C. The potassium salt was obtained from this phenol as a very pale yellow solid. Two liquid phases remained throughout the reaction twice extracted with diethyl ether to recover non-phenolic material (9 g) the phenolic component (86 g; m.p. 150°-154° C) was extracted with more ether at 180° C followed by recrystallisation from toluene (400 cm3)

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

Procedure: 5 mmol of sodium 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanolate and 10 mmol of bis(4-fluorophenyl) sulphone are treated as described in Example 61 (method A).

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

Procedure: A 194 g (1.1 moles) quantity of 4-fluorobenzenesulfonic acid was added to 96 g (1 mole) of fluorobenzene and the mixture was cooled with water while 123 g (1.1 moles) of chlorosulfonic acid was added at about 10° to about 20° C. over a period of 1 hour. After the addition, the reaction mixture was stirred for 3 hours while being maintained at 20° to 30° C. The hydrochloric acid gas evolved during the reaction was continuously removed from the reaction system. After the completion of the reaction, about 400 ml of water was added to the reaction mixture, and 9.6 g (0.1 mole) of the unreacted fluorobenzene was recovered by distillation. Separation of the precipitate by filtration gave 65 g of 4,4'-difluorodiphenylsulfone in 58% yield. M.P. 97° to 98° C. Purity of 99.7%. was added at about 10° to about 20° C. over a period of 1 hour After the addition while being maintained at 20° to 30° C was continuously removed from the reaction system After the completion of the reaction, about 400 ml of water was recovered by distillation Separation of the precipitate by filtration

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (427 mg; 2.13 mmol), bis(4-fluorophenyl) sulfone (493 mg; 1.94 mmol) and potassium carbonate (1.01 g; 7.76 mmol) in dimethylsulfoxide (5 mL) is heated over night at 100° C. The temperature is then increased to 120° C. and the mixture is reacted at this temperature for 24 hours. The reaction is then diluted with dichloromethane (100 mL), filtered and the filtrate is washed with aq. 1N hydrochloric acid (2×20 mL), and water (2×20 mL). The organic layer is dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue obtained is finally purified by column chromatography on silica gel (dichloromethane:methanol 100:0 (200 mL) and then 98:2 (150 mL)) to afford the desired product (653 mg; 1.50 mmol). the mixture is reacted at this temperature for 24 hours filtered the filtrate is washed with aq. 1N hydrochloric acid (2×20 mL), and water (2×20 mL) The organic layer is dried over magnesium sulfate filtered concentrated under reduced pressure The residue obtained is finally purified by column chromatography on silica gel (dichloromethane:methanol 100:0 (200 mL)

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

Procedure: Bis-(4-fluorophenyl) sulphone (100 g; 0.394 mole), potassium hydroxide solution (91.98 g; 0.787 mole KOH) and dimethyl sulphoxide (400 cm3) were stirred together in a stainless steel vessel under nitrogen at 57° C. for 24 hours. Two liquid phases remained throughout the reaction. The reaction mixture was diluted with water and twice extracted with diethyl ether to recover non-phenolic material (9 g). The aqueous phase was then acidified and the phenolic component (86 g; m.p. 150°-154° C.) was extracted with more ether. By subliming this product under a diffusion pump at 180° C., followed by recrystallisation from toluene (400 cm3), 4-(4-fluorophenylsulphonyl)phenol (72.5 g) was obtained, m.p. 158°-159° C. The potassium salt was obtained from this phenol as a very pale yellow solid. Two liquid phases remained throughout the reaction twice extracted with diethyl ether to recover non-phenolic material (9 g) the phenolic component (86 g; m.p. 150°-154° C.) was extracted with more ether at 180° C. followed by recrystallisation from toluene (400 cm3)