1,3,5-trichloro-2,4,6-trifluorobenzene

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a N2 atmosphere 29.5 g of 1,3,5-trichloro-2,4,6-trifluorobenzene (Oakwood Products, Inc.) were dissolved in 150 mL dry ethyl ether. The solution was cooled to −78° C. in an acetone/dry-ice bath, then treated with 62.7 mL n-butyllithium (2 M solution in hexanes) over a two-hour period. Stirring was continued for 3 hours at −78° C. Via syringe, 34.8 g perfluorocyclohexanone were added, and the mixture was stirred at room temperature for 16 hours. The reaction was quenched with dilute HCl and extracted with ethyl ether, and the extracts were dried (using MgSO4) and rotary evaporated. Vacuum distillation (118-120° C., 80-110 Pa) gave 37.3 g 1-(3,5-dichloro-2,4,6-trifluorophenyl) perfluorocyclohexanol (62% yield) as a colorless liquid. the mixture was stirred at room temperature for 16 hours The reaction was quenched with dilute HCl extracted with ethyl ether the extracts were dried (using MgSO4) and rotary evaporated Vacuum distillation (118-120° C., 80-110 Pa)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a N2 atmosphere 29.5 g of 1,3,5-trichloro-2,4,6-trifluorobenzene (Oakwood Products, Inc.) were dissolved in 150 mL dry ethyl ether. The solution was cooled to −78° C. in an acetone/dry-ice bath, then treated with 62.7 mL n-butyllithium (2 M solution in hexanes) over a two-hour period. Stirring was continued for 3 hours at −78° C. Via syringe, 34.8 g perfluorocyclohexanone were added, and the mixture was stirred at room temperature for 16 hours. The reaction was quenched with dilute HCl and extracted with ethyl ether, and the extracts were dried (using MgSO4) and rotary evaporated. Vacuum distillation (118-120° C., 80-110 Pa) gave 37.3 g 1-(3,5-dichloro-2,4,6-trifluorophenyl) perfluorocyclohexanol (62% yield) as a colorless liquid. the mixture was stirred at room temperature for 16 hours The reaction was quenched with dilute HCl extracted with ethyl ether the extracts were dried (using MgSO4) and rotary evaporated Vacuum distillation (118-120° C., 80-110 Pa)

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Palladium on carbon (10%, 300 mg), aqueous sodium hydroxide solution (35% strength, 26.5 g, 232 mmol, 3.7 equivalents), 62 g of water and 1,3,5-trichloro-2,4,6-trifluorobenzene (15 g, 62 mmol) were placed in a pressure vessel. After flushing with nitrogen, the pressure vessel was heated to 140° C. and pressurized with 30 bar of hydrogen. A hydrogen pressure of 30 bar was maintained at 140° C. for 12 hours. After cooling to 20-25° C., the pressure vessel was depressurized. The reaction solution was subjected to an azeotropic distillation via a distillation attachment; the distillate went over at a temperature of 99.5° C. After separation of the phases, the lower organic phase comprised the title compound. Washing with water and drying gave 8.05 g of 1,3,5-trifluorobenzene (98% of theory). After flushing with nitrogen A hydrogen pressure of 30 bar was maintained at 140° C. for 12 hours After cooling to 20-25° C. The reaction solution was subjected to an azeotropic distillation via a distillation attachment went over at a temperature of 99.5° C After separation of the phases Washing with water drying

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Palladium on carbon (10%, 410 mg), 100 g of water, 21.8 g of 1,3,5-trichloro-2,4,6-trifluorobenzene and 32.9 g of sodium acetate (4.5 equivalents) were placed in a pressure vessel. After flushing with nitrogen, the pressure vessel was heated to 140° C. and pressurized with 12 bar of hydrogen. A hydrogen pressure of 12 bar was maintained at 140° C. for about 12 hours while stirring vigorously. After cooling to 20-25° C., the pressure vessel was depressurized. The two-phase reaction solution was filtered and the phases were then separated. This gave a yield of 88.2% of 1,3,5-trifluorobenzene. After flushing with nitrogen A hydrogen pressure of 12 bar was maintained at 140° C. for about 12 hours After cooling to 20-25° C. The two-phase reaction solution was filtered the phases were then separated

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

Procedure: In Russ. J. of Org. Chem., vol. 36, 1, pp. 132-33 (2000) describes the dehalogenation of 1,3,5-trichlorotrifluorobenzene by means of zinc in the presence of NiCl2 and bipyridine to give 1,3,5-trifluorobenzene.

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a N2 atmosphere 29.5 g of 1,3,5-trichloro-2,4,6-trifluorobenzene (Oakwood Products, Inc.) were dissolved in 150 mL dry ethyl ether. The solution was cooled to -78° C. in an acetone/dry-ice bath, then treated with 62.7 mL n-butyllithium (2 M solution in hexanes) over a two-hour period. Stirring was continued for 3 hours at -78° C. Via syringe, 34.8 g perfluorocyclohexanone were added, and the mixture was stirred at room temperature for 16 hours. The reaction was quenched with dilute HCl and extracted with ethyl ether, and the extracts were dried (using MgSO4) and rotary evaporated. Vacuum distillation (118-120° C., 80-110 Pa) gave 37.3 g 1-(3,5-dichloro-2,4,6-trifluorophenyl) perfluorocyclohexanol (62% yield) as a colorless liquid. the mixture was stirred at room temperature for 16 hours The reaction was quenched with dilute HCl extracted with ethyl ether the extracts were dried (using MgSO4) and rotary evaporated Vacuum distillation (118-120° C., 80-110 Pa)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a N2 atmosphere 29.5 g of 1,3,5-trichloro-2,4,6-trifluorobenzene (Oakwood Products, Inc.) were dissolved in 150 mL dry ethyl ether. The solution was cooled to -78° C. in an acetone/dry-ice bath, then treated with 62.7 mL n-butyllithium (2 M solution in hexanes) over a two-hour period. Stirring was continued for 3 hours at -78° C. Via syringe, 34.8 g perfluorocyclohexanone were added, and the mixture was stirred at room temperature for 16 hours. The reaction was quenched with dilute HCl and extracted with ethyl ether, and the extracts were dried (using MgSO4) and rotary evaporated. Vacuum distillation (118-120° C., 80-110 Pa) gave 37.3 g 1-(3,5-dichloro-2,4,6-trifluorophenyl) perfluorocyclohexanol (62% yield) as a colorless liquid. the mixture was stirred at room temperature for 16 hours The reaction was quenched with dilute HCl extracted with ethyl ether the extracts were dried (using MgSO4) and rotary evaporated Vacuum distillation (118-120° C., 80-110 Pa)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a N2 atmosphere 29.5 g of 1,3,5-trichloro-2,4,6-trifluorobenzene (Oakwood Products, Inc.) were dissolved in 150 mL dry ethyl ether. The solution was cooled to −78° C. in an acetone/dry-ice bath, then treated with 62.7 mL n-butyllithium (2 M solution in hexanes) over a two-hour period. Stirring was continued for 3 hours at −78° C. Via syringe, 34.8 g perfluorocyclohexanone were added, and the mixture was stirred at room temperature for 16 hours. The reaction was quenched with dilute HCl and extracted with ethyl ether, and the extracts were dried (using MgSO4) and rotary evaporated. Vacuum distillation (118-120° C., 80-110 Pa) gave 37.3 g 1-(3,5-dichloro-2,4,6-trifluorophenyl)perfluorocyclohexanol (62% yield) as a colorless liquid. the mixture was stirred at room temperature for 16 hours The reaction was quenched with dilute HCl extracted with ethyl ether the extracts were dried (using MgSO4) and rotary evaporated Vacuum distillation (118-120° C., 80-110 Pa)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a N2 atmosphere 29.5 g of 1,3,5-trichloro-2,4,6-trifluorobenzene (Oakwood Products, Inc.) were dissolved in 150 mL dry ethyl ether. The solution was cooled to −78° C. in an acetone/dry-ice bath, then treated with 62.7 mL n-butyllithium (2 M solution in hexanes) over a two-hour period. Stirring was continued for 3 hours at −78° C. Via syringe, 34.8 g perfluorocyclohexanone were added, and the mixture was stirred at room temperature for 16 hours. The reaction was quenched with dilute HCl and extracted with ethyl ether, and the extracts were dried (using MgSO4) and rotary evaporated. Vacuum distillation (118-120° C., 80-110 Pa) gave 37.3 g 1-(3,5-dichloro-2,4,6-trifluorophenyl)perfluorocyclohexanol (62% yield) as a colorless liquid. the mixture was stirred at room temperature for 16 hours The reaction was quenched with dilute HCl extracted with ethyl ether the extracts were dried (using MgSO4) and rotary evaporated Vacuum distillation (118-120° C., 80-110 Pa)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a N2 atmosphere 29.5 g of 1,3,5-trichloro-2,4,6-trifluorobenzene (Oakwood Products, Inc.) were dissolved in 150 mL dry ethyl ether. The solution was cooled to −78° C. in an acetone/dry-ice bath, then treated with 62.7 mL n-butyllithium (2 M solution in hexanes) over a two-hour period. Stirring was continued for 3 hours at −78° C. Via syringe, 34.8 g perfluorocyclohexanone were added, and the mixture was stirred at room temperature for 16 hours. The reaction was quenched with dilute HCl and extracted with ethyl ether, and the extracts were dried (using MgSO4) and rotary evaporated. Vacuum distillation (118-120° C., 80-110 Pa) gave 37.3 g 1-(3,5-dichloro-2,4,6-trifluorophenyl) perfluorocyclohexanol (62% yield) as a colorless liquid. the mixture was stirred at room temperature for 16 hours The reaction was quenched with dilute HCl extracted with ethyl ether the extracts were dried (using MgSO4) and rotary evaporated Vacuum distillation (118-120° C., 80-110 Pa)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under a N2 atmosphere 29.5 g of 1,3,5-trichloro-2,4,6-trifluorobenzene (Oakwood Products, Inc.) were dissolved in 150 mL dry ethyl ether. The solution was cooled to −78° C. in an acetone/dry-ice bath, then treated with 62.7 mL n-butyllithium (2 M solution in hexanes) over a two-hour period. Stirring was continued for 3 hours at −78° C. Via syringe, 34.8 g perfluorocyclohexanone were added, and the mixture was stirred at room temperature for 16 hours. The reaction was quenched with dilute HCl and extracted with ethyl ether, and the extracts were dried (using MgSO4) and rotary evaporated. Vacuum distillation (118-120° C., 80-110 Pa) gave 37.3 g 1-(3,5-dichloro-2,4,6-trifluorophenyl) perfluorocyclohexanol (62% yield) as a colorless liquid. the mixture was stirred at room temperature for 16 hours The reaction was quenched with dilute HCl extracted with ethyl ether the extracts were dried (using MgSO4) and rotary evaporated Vacuum distillation (118-120° C., 80-110 Pa)

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Palladium on carbon (10%, 300 mg), aqueous sodium hydroxide solution (35% strength, 26.5 g, 232 mmol, 3.7 equivalents), 62 g of water and 1,3,5-trichloro-2,4,6-trifluorobenzene (15 g, 62 mmol) were placed in a pressure vessel. After flushing with nitrogen, the pressure vessel was heated to 140° C. and pressurized with 30 bar of hydrogen. A hydrogen pressure of 30 bar was maintained at 140° C. for 12 hours. After cooling to 20-25° C., the pressure vessel was depressurized. The reaction solution was subjected to an azeotropic distillation via a distillation attachment; the distillate went over at a temperature of 99.5° C. After separation of the phases, the lower organic phase comprised the title compound. Washing with water and drying gave 8.05 g of 1,3,5-trifluorobenzene (98% of theory). After flushing with nitrogen A hydrogen pressure of 30 bar was maintained at 140° C. for 12 hours After cooling to 20-25° C. The reaction solution was subjected to an azeotropic distillation via a distillation attachment went over at a temperature of 99.5° C After separation of the phases Washing with water drying