1,4-Dibromo-2-chloro-1,1,2-trifluorobutane

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

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

Procedure: A supply of BCTFB was obtained by reacting ethylene with dibrominated CTFE in 1,1,1,3,3-pentafluorobutane at 120° C. for 4 hours using a mixture of tert-butyl peroxypivalate (TBPPi, 3 mol %) and 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane (Trigonox 101, 4.5 mol %) as radical initiators, with the resulting structure being Br—CF2—CFCl—CH2—CH2—Br after distillation under vacuum. This was dehydrochlorinated with KOH in refluxing methanol for 15 hours, forming Br—CF2—CFCl—CH═CH2 (BCTFB). Successful radical copolymerization of CTFE (96 mol % in the feed) with BCTFB initiated by TBPPi (2 mol % with respect to both monomers) was carried out at 74° C. in a 100 mL autoclave. The 19F NMR spectrum of the obtained polymer is shown in FIG. 7. A supply of BCTFB was obtained at 120° C. for 4 hours after distillation under vacuum in refluxing methanol for 15 hours

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,4-dibromo-2-chloro-1,1,2-trifluorobutane (XVI) (7.5 g, 24.6 mmol), 1-methyl-2-pyrrolidinone (14 mL) and water (2.5 mL) was heated at 130° C. for 16 hours. The mixture was cooled to room temperature, diluted with water (80 mL) and extracted with ether (2×75 mL). The ether extract was washed with water (31×40 mL), brine, and dried over anhydrous magnesium sulfate. The residue obtained after evaporation of the solvent was chromatographed over silica gel to give 2.9 g (49%) of the desired alcohol as a clear oil. The mixture was cooled to room temperature extracted with ether (2×75 mL) The ether extract was washed with water (31×40 mL), brine dried over anhydrous magnesium sulfate The residue obtained after evaporation of the solvent was chromatographed over silica gel

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,4-dibromo-2-chloro-1,1,2-trifluorobutane (XVI) (7.5 g, 24.6 mmol), 1-methyl-2-pyrrolidinone (14 mL) and water (2.5 mL) was heated at 130° C. for 16 hours. The mixture was cooled to room temperature, diluted with water (80 mL) and extracted with ether (2×75 mL). The ether extract was washed with water (31×40 mL), brine, and dried over anhydrous magnesium sulfate. The residue obtained after evaporation of the solvent was chromatographed over silica gel to give 2.9 g (49%) of the desired alcohol as a clear oil. The mixture was cooled to room temperature extracted with ether (2×75 mL) The ether extract was washed with water (31×40 mL), brine dried over anhydrous magnesium sulfate The residue obtained after evaporation of the solvent was chromatographed over silica gel

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

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

Procedure: A supply of BCTFB was obtained by reacting ethylene with dibrominated CTFE in 1,1,1,3,3-pentafluorobutane at 120° C. for 4 hours using a mixture of tert-butyl peroxypivalate (TBPPi, 3 mol %) and 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane (Trigonox 101, 4.5 mol %) as radical initiators, with the resulting structure being Br—CF2—CFCl—CH2—CH2—Br after distillation under vacuum. This was dehydrochlorinated with KOH in refluxing methanol for 15 hours, forming Br—CF2—CFCl—CH═CH2 (BCTFB). Successful radical copolymerization of CTFE (96 mol % in the feed) with BCTFB initiated by TBPPi (2 mol % with respect to both monomers) was carried out at 74° C. in a 100 mL autoclave. The 19F NMR spectrum of the obtained polymer is shown in FIG. 7. A supply of BCTFB was obtained at 120° C. for 4 hours after distillation under vacuum in refluxing methanol for 15 hours

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,4-dibromo-2-chloro-1,1,2-trifluorobutane (XVI) (7.5 g, 24.6 mmol), 1-methyl-2-pyrrolidinone (14 mL) and water (2.5 mL) was heated at 130° C. for 16 hours. The mixture was cooled to room temperature, diluted with water (80 mL) and extracted with ether (2×75 mL). The ether extract was washed with water ( 3×40 mL), brine, and dried over anhydrous magnesium sulfate. The residue obtained after evaporation of the solvent was chromatographed over silica gel to give 2.9 g (49%) of the desired alcohol as a clear oil. The mixture was cooled to room temperature extracted with ether (2×75 mL) The ether extract was washed with water ( 3×40 mL), brine dried over anhydrous magnesium sulfate The residue obtained after evaporation of the solvent was chromatographed over silica gel

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,4-dibromo-2-chloro-1,1,2-trifluorobutane (XVI) (7.5 g, 24.6 mmol), 1-methyl-2-pyrrolidinone (14 mL) and water (2.5 mL) was heated at 130° C. for 16 hours. The mixture was cooled to room temperature, diluted with water (80 mL) and extracted with ether (2×75 mL). The ether extract was washed with water ( 3×40 mL), brine, and dried over anhydrous magnesium sulfate. The residue obtained after evaporation of the solvent was chromatographed over silica gel to give 2.9 g (49%) of the desired alcohol as a clear oil. The mixture was cooled to room temperature extracted with ether (2×75 mL) The ether extract was washed with water ( 3×40 mL), brine dried over anhydrous magnesium sulfate The residue obtained after evaporation of the solvent was chromatographed over silica gel

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,4-dibromo-2-chloro-1,1,2-trifluorobutane (XVI) (7.5 g, 24.6 mmol), 1-methyl-2-pyrrolidinone (14 mL) and water (2.5 mL) was heated at 130° C. for 16 hours. The mixture was cooled to room temperature, diluted with water (80 mL) and extracted with ether (2×75 mL). The ether extract was washed with water (3×40 mL), brine, and dried over anhydrous magnesium sulfate. The residue obtained after evaporation of the solvent was chromatographed over silica gel to give 2.9 g (49%) of the desired alcohol as a clear oil. The mixture was cooled to room temperature extracted with ether (2×75 mL) The ether extract was washed with water (3×40 mL), brine dried over anhydrous magnesium sulfate The residue obtained after evaporation of the solvent was chromatographed over silica gel

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,4-dibromo-2-chloro-1,1,2-trifluorobutane (XVI) (7.5 g, 24.6 mmol), 1-methyl-2-pyrrolidinone (14 mL) and water (2.5 mL) was heated at 130° C. for 16 hours. The mixture was cooled to room temperature, diluted with water (80 mL) and extracted with ether (2×75 mL). The ether extract was washed with water (3×40 mL,), brine, and dried over anhydrous magnesium sulfate. The residue obtained after evaporation of the solvent was chromatographed over silica gel to give 2.9 g (49%) of the desired alcohol as a clear off. The mixture was cooled to room temperature extracted with ether (2×75 mL) The ether extract was washed with water (3×40 mL,), brine dried over anhydrous magnesium sulfate The residue obtained after evaporation of the solvent was chromatographed over silica gel

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

Procedure: 1.2 g of 2-(2,2,3,4,4,4-hexafluorobutyl)malononitrile and 1.5 g of 2-chloro-1,4-dibromo-1,1,2-trifluorobutane were dissolved in 10 ml of dimethyl sulfoxide, 0.7 g of potassium carbonate was added, and the mixture was stirred at room temperature for 5 hours. Thereafter, dilute hydrochloric acid was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed successively with water and aqueous saturated sodium chloride, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.14 g of 2-(4-bromo-3-chloro-3,4,4-trifluorobutyl)-2-(2,2,3,4,4,4-hexafluorobutyl)malononitrile (hereinafter, referred to as the present compound (46)). followed by extraction with ethyl acetate The organic layer was washed successively with water and aqueous saturated sodium chloride dried over anhydrous magnesium sulfate concentrated under reduced pressure

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,4-dibromo-2-chloro-1,1,2-trifluorobutane (XVI) (7.5 g, 24.6 mmol), 1-methyl-2-pyrrolidinone (14 mL) and water (2.5 mL) was heated at 130° C. for 16 hours. The mixture was cooled to room temperature, diluted with water (80 mL) and extracted with ether (2×75 mL). The ether extract was washed with water (31×40 mL), brine, and dried over anhydrous magnesium sulfate. The residue obtained after evaporation of the solvent was chromatographed over silica gel to give 2.9 g (49%) of the desired alcohol as a clear oil. The mixture was cooled to room temperature extracted with ether (2×75 mL) The ether extract was washed with water (31×40 mL), brine dried over anhydrous magnesium sulfate The residue obtained after evaporation of the solvent was chromatographed over silica gel