1,1,1-trichloro-2,2,2-trifluoroethane

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: Then, 19.54 g of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde was dissolved in 200 ml of N,N-dimethylformamide, to which 25.3 g of 1,1,1-trichlorotrifluoroethane, 17.6 g of zinc dust and 2.0 g of aluminum chloride were added. After stirring at room temperature for 1.5 hours, the reaction mixture was filtered. The filtrate was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 8.46 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-chloro-4,4-difluoro-2-hydoxy-3-butenyloxy)butyloxy)benzene (yield, 38%), nD22.5 1.5302. were added the reaction mixture was filtered The filtrate was poured into diluted hydrochloric acid extracted twice with diethyl ether washed with water dried over magnesium sulfate concentrated to give a crude product

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

Procedure: To a mixture of 0.12 g of aluminum chloride and 50 ml of N,N-dimethylformamide was added 3.04 g of 1,1,1-trichlorotrifluoroethane. After stirring at room temperature for 1 hour, 1.21 g of 5-(2,6-diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde was added, and the reaction mixture was further stirred at room temperature for 4 hours, to which 1.38 g of acetic anhydride was added. After stirring at room temperature for 1 hour, 0.88 g of zinc dust was added, and the reaction mixture was stirred at room temperature for 12 hours and filtered. The filtrate was poured into 50 ml of diluted hydrochloric acid and extracted twice with 100 ml of diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then evaporated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 2.91 g of (Z)-3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzene (yield, 72%), nD26.0 1.4958. was added After stirring at room temperature for 1 hour the reaction mixture was stirred at room temperature for 12 hours filtered The filtrate was poured into 50 ml of diluted hydrochloric acid extracted twice with 100 ml of diethyl ether washed with water dried over magnesium sulfate evaporated to give a crude product

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

Procedure: To a mixture of 2.01 g of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde, 1.31 g of zinc dust and 10 ml of N,N-dimethylformamide was added 4.12 g of 1,1,1-trichlorotrifluoroethane. After stirring at room temperature for 1.5 hours, the reaction mixture was filtered. The filtrate was poured into 20 ml of diluted hydrochloric acid and extracted twice with 50 ml of ethyl acetate. The ethyl acetate layers were combined, washed with water, dried over magnesium sulfate and then evaporated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 1.76 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3,3-dichloro-4,4,4-trifluoro-2-hydroxybutyloxy)butyloxy)benzene (yield, 63%), nD24.2 1.5188. the reaction mixture was filtered The filtrate was poured into 20 ml of diluted hydrochloric acid extracted twice with 50 ml of ethyl acetate washed with water dried over magnesium sulfate evaporated to give a crude product

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

Procedure: To a mixture of 1.21 g of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde, 0.57 g of zinc dust and 10 ml of N,N-dimethylformamide was added 0.82 g of 1,1,1-trichlorotrifluoroethane. After stirring at room temperature for 1.5 hours, 0.44 g of acetic anhydride was added. The reaction mixture was stirred at room temperature for 3 hours and then filtered. The filtrate was poured into 20 ml of diluted hydrochloric acid and extracted twice with 50 ml of diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then evaporated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.21 g of (Z)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzene [the integrated CF3 signal ratio of Z/E=94/6 as determined by 19F-NMR (CDCl3 /CFCl3)] (yield, 14%), nD26.5 1.5123. The reaction mixture was stirred at room temperature for 3 hours filtered The filtrate was poured into 20 ml of diluted hydrochloric acid extracted twice with 50 ml of diethyl ether washed with water dried over magnesium sulfate evaporated to give a crude product

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3 g of 2,6-dichloro-4-nitro benzaldehyde were reacted, in 20 ml of anhydrous DMF under a nitrogen atmosphere, with CF3CCl2ZnCl prepared from 5 g of CF3CCl3 and 2.2 g of Zn in 10 ml of THF at 60° C. for 1 hour. The mixture was heated at 50° C. for 2 hours and at the end of the reaction it was poured into acidulated water and extracted repeatedly with ethyl ether. was poured extracted repeatedly with ethyl ether

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1,1,1-trifluoro-2,2,2-trichloroethane and tert-butylvinyl ether in a 3:1 molar ratio is introduced to a jacketed photochemical reaction vessel. The mixture is irradiated using a medium-pressure mercury UV lamp so as to maintain the temperature of the mixture at about 35-45° C. for about 2 hours. The resultant reaction mixture is concentrated to remove volatiles and distilled to produce 3-chloro-4,4,4-trifluorobut-2-enal in a 60% yield. 1 molar ratio is introduced to a jacketed photochemical reaction vessel The mixture is irradiated The resultant reaction mixture is concentrated to remove volatiles distilled

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

Procedure: Into the experimental apparatus described in Example 1, 2 g HgSO4 and 10 g BBr3 are added. A solution of 93.7 g CF3CCl3, 162 g SO3 and 4 g H2SO4 are added in drops. The trifluoroacetylchloride leaving the reflux condenser is passed through a wash flask with H2SO4 and subsequently fed into a reaction vessel with ethanol. In the process, trifluoracetic acid ethylester is formed. are added

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

Procedure: Into the experimental apparatus described in Example 1, 2 g HgSO4 and 10 g BBr3 are added. A solution of 93.7 g CF3CCl3, 162 g SO3 and 4 g H2SO4 are added in drops. The trifluoroacetylchloride leaving the reflux condenser is passed through a wash flask with H2SO4 and subsequently fed into a reaction vessel with ethanol. In the process, trifluoracetic acid ethylester is formed. are added

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

Procedure: Then, 19.54 g of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde was dissolved in 200 ml of N,N-dimethylformamide, to which 25.3 g of 1,1,1-trichlorotrifluoroethane, 17.6 g of zinc dust and 2.0 g of aluminum chloride were added. After stirring at room temperature for 1.5 hours, the reaction mixture was filtered. The filtrate was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 8.46 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-chloro-4,4-difluoro-2-hydoxy-3-butenyloxy)butyloxy)benzene (yield, 38%), nD22.5 1.5302. were added the reaction mixture was filtered The filtrate was poured into diluted hydrochloric acid extracted twice with diethyl ether washed with water dried over magnesium sulfate concentrated to give a crude product