Tetrafluoroisophthalonitrile

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

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

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

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

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

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

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

Procedure: By a method similar to Example 11, a reaction was carried out using 2,4,5,6-tetrafluoroisophthalonitrile, instead of 3,4,5,6-tetrafluorophthalonitrile. After 5 hours, the reaction solution was analyzed by gas chromatography, whereupon the conversion of 2,4,5,6-tetrafluoroisophthalonitrile was found to be 36% and the yield of 2,3,4,6-tetrafluorobenzonitrile (based on 2,4,5,6-tetrafluoroisophthalonitrile) was 20%. At the same time, 1.1 mmol of α-methylbenzylcyanide was produced. This corresponded to 0.35 times molar amount relative to the production of 2,3,4,6-tetrafluorobenzonitrile.

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

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

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

Procedure: In a 3 liter reaction vessel, were added 200 g (1.00 mol) of tetrafluoroisophthalonitrile, 1 liter of N-dimethylformamide (DMF) and 102.7 g (1.00 mol) of sodium bromide (NaBr). This mixture was heated at 120° C. for 1 hour. Separately, 3 liter of water was poured to a 5 liter of beaker, and to which was poured the resulting reaction solution. After suction filtration, the residue was washed with water and hexane, and then dried in vacuo to offer 198.2 g of a white solid. The solid was purified by means of solid distillation to give 142.8 g (0.55 mol) of 4-bromo-2,5,6-trifluoroisophthalonitrile as a white solid (yield: 55%). In a 3 liter reaction vessel to which was poured the resulting reaction solution After suction filtration the residue was washed with water and hexane dried in vacuo The solid was purified by means of solid distillation

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

Procedure: In a 3 liter reaction vessel, were added 200 g (1.00 mol) of tetrafluoroisophthalonitrile, 1 liter of N-dimethylformamide (DMF) and 102.7 g (1.00 mol) of sodium bromide (NaBr). This mixture was heated at 120° C. for 1 hour. Separately, 3 liter of water was poured to a 5 liter of beaker, and to which was poured the resulting reaction solution. After suction filtration, the residue was washed with water and hexane, and then dried in vacuo to offer 198.2 g of a white solid. The solid was purified by means of solid distillation to give 142.8 g (0.55 mol) of 4-bromo-2,5,6-trifluoroisophthalonitrile as a white solid (yield: 55%). In a 3 liter reaction vessel to which was poured the resulting reaction solution After suction filtration the residue was washed with water and hexane dried in vacuo The solid was purified by means of solid distillation

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

Procedure: By a method similar to Example 11, a reaction was carried out using 2,4,5,6-tetrafluoroisophthalonitrile, instead of 3,4,5,6-tetrafluorophthalonitrile. After 5 hours, the reaction solution was analyzed by gas chromatography, whereupon the conversion of 2,4,5,6-tetrafluoroisophthalonitrile was found to be 36% and the yield of 2,3,4,6-tetrafluorobenzonitrile (based on 2,4,5,6-tetrafluoroisophthalonitrile) was 20%. At the same time, 1.1 mmol of α-methylbenzylcyanide was produced. This corresponded to 0.35 times molar amount relative to the production of 2,3,4,6-tetrafluorobenzonitrile.