3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline

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

Procedure: 33.4 g of 3,5-dichloro-4-(1,1,2,2,-tetrafluoroethoxy)aniline are dissolved in 130 ml of chlorobenzene. With stirring, this solution is added dropwise at 22° C. to a solution consisting of 90 g of toluene containing 20% by weight of phosgene and of 100 ml of dioxane and 300 ml of chlorobenzene. The reaction mixture is stirred for 1 hour at room temperature, 1 hour at 50° C. and then 1 hour at 80° C. The reaction mixture is subsequently concentrated in a water-jet vacuum and then distilled under high vacuum, affording the title compound of the formula ##STR8## as a colourless oil. Boiling point 81°-83° C./2.5 mbar. this solution is added dropwise at 22° C. to a solution The reaction mixture is stirred for 1 hour at room temperature, 1 hour at 50° C. 1 hour at 80° C The reaction mixture is subsequently concentrated in a water-jet vacuum distilled under high vacuum

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

Procedure: A solution of 3.5 mmol of 2-(4-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propionyl chloride in 15 ml of methylene chloride was added dropwise to an ice-cooled solution prepared from 1.22 g (3.5 mmol) of an 80 percent solution of 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline in DMF, 0.42 g (4.2 mmol) of triethylamine and 40 ml of methylene chloride. The reaction mixture was stirred at room temperature overnight and then poured into a dilute aqueous HCl solution. The organic layer was separated, washed with a saturated aqueous NaHCO3 solution, dried over MgSO4 and evaporated to dryness. The residual material, a gum, was purified by preparative scale liquid chromatography, eluting with an 86:14 hexane:acetone mixture. After removal of the solvent, there was left 1.02 g (47 percent of theoretical) of the above-named product as a light yellow glassy material. The structure of the product was confirmed by its IR and NMR spectrum (NMR Spectrum: (d6 -DMSO); 8.55 (br, m, 1H); 8.45 (br, 1H); 7.9 (s, 2H); 6.6-7.2 (m, 5H); 4.9 (q, 1H); 1.6 (d, 3H). (Compound 2) cooled solution The organic layer was separated washed with a saturated aqueous NaHCO3 solution dried over MgSO4 evaporated to dryness The residual material, a gum, was purified by preparative scale liquid chromatography eluting with an 86:14 hexane After removal of the solvent, there was left 1.02 g (47 percent of theoretical) of the above-named product as a light yellow glassy material