1,1,1,2,2-pentafluoro-4-iodobutane

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:

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

Procedure: To a suspension of 22.85 g of potassium thioacetate in 200 ml of methanol was added dropwise 54.79 g of 1-iodo-3,3,4,4,4-pentafluorobutane at 0° C. over 30 minutes under a nitrogen atmosphere, and the mixture was stirred at room temperature for 1 hour. At this time, the reaction mixture was analyzed by thin layer chromatography (TLC), and thereby the formation of 3,3,4,4,4-pentafluorobutyl thioacetate was confirmed. After the mixture was cooled to 0° C., 40.52 g of a 28% solution of sodium methoxide in methanol was added dropwise over 15 minutes thereto. The mixture was stirred at room temperature for 1 hour. To the mixture was added 16.61 g of chloroacetonitrile at 0° C., and the mixture was stirred at room temperature for 3 hours. A reaction vessel was cooled in an ice bath, and an aqueous 1N hydrochloric acid solution was added to the reaction mixture. Methanol was distilled off under reduced pressure. The residual reaction mixture was extracted with 200 ml of t-butyl methyl ether twice. Organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over sodium sulfate, filtered, and then subjected to reduced pressure to distill off the solvent. The residue was subjected to silica gel column chromatography to obtain 17.81 g of (3,3,4,4,4-pentafluorobutylthio)acetonitrile. After the mixture was cooled to 0° C. The mixture was stirred at room temperature for 1 hour the mixture was stirred at room temperature for 3 hours A reaction vessel was cooled in an ice bath Methanol was distilled off under reduced pressure The residual reaction mixture was extracted with 200 ml of t-butyl methyl ether twice washed with an aqueous saturated sodium chloride solution dried over sodium sulfate filtered to distill off the solvent

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

Procedure: Using 1.00 g of (4-chlorobenzyl)malononitrile, 10 ml of N,N-dimethylformamide, 0.21 g of sodium hydride (60% in oil), and 1.44 g of 4-iodo-1,1,1,2,2-pentafluorobutane, and according to the process described in the Production Example 1, there was obtained 0.47 g of 2-(4-chlorobenzyl)-2-(3,3,4,4,4-pentafluorobutyl)malononitrile (the present compound (23)).

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

Procedure: Using 0.30 g of (4-(trifluoromethoxy)benzyl)malononitrile, 10 ml of N,N-dimethylformamide, 0.06 g of sodium hydride (60% in oil), and 0.38 g of 4-iodo-1,1,1,2,2-pentafluorobutane, and according to the process described in the Production Example 1, there was obtained 0.15 g of 2-(3,3,4,4,4-pentafluorobutyl)-2-(4-(trifluoromethoxy)benzyl)malononitrile (the present compound (10)).

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

Procedure: Using 0.30 g of (4-(trifluoromethoxy)benzyl)malononitrile, 10 ml of N,N-dimethylformamide, 0.06 g of sodium hydride (60% in oil), and 0.38 g of 4-iodo-1,1,1,2,2-pentafluorobutane, and according to the process described in the Production Example 1, there was obtained 0.15 g of 2-(3,3,4,4,4-pentafluorobutyl)-2-(4-(trifluoromethoxy)benzyl)malononitrile (the present compound (10)).

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

Procedure: Using 0.30 g of (4-(trifluoromethyl)benzyl)malononitrile, 6 ml of N,N-dimethylformamide, 0.60 g of sodium hydride (60% in oil), and 0.38 g of 4-iodo-1,1,1,2,2-pentafluorobutane, and according to the process described in the Production Example 1, there was obtained 0.30 g of 2-(3,3,4,4,4-pentafluorobutyl)-2-(4-(trifluoromethyl)benzyl)malononitrile (the present compound (8)).