Hexachloroethane → 2-(3-Nitrophenoxy)-1-chloro-1,2,2-trifluoro-1-(1,1,2,2,3,3,3-heptafluoropropoxy)ethane

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Reaction Steps

To a mixture of 19.3 g (0.072 mol) of perfluoropropyl perfluorovinyl ether and 16.3 g (0.069 mol) of hexachloroethane in 25 mL of dimethylformamide (DMF) at about 0° C. under argon was added 6.85 g (0.043 mol) of solid sodium 3-nitrophenoxide over 14 min. The solid was rinsed into the flask with an additional 15 mL of DMF. The mixture was allowed to warm to room temperature and stirred for about 3 days. It was then poured into ice water containing 5 mL of concentrated hydrochloric acid and extracted with 2×100 mL of ether. The combined ether extracts were washed with 2×50 mL of water and dried over anhydrous magnesium sulfate. The solution was concentrated on a rotary evaporator and then distilled in a Kugelrohr apparatus. After removing lower boiling materials, the product was distilled at a bath temperature of 85°-95° C. and 0.5 mm pressure to give 16.6 g (89%) of 3-(perfluoro-2-chloro-3-oxahexyloxy)nitrobenzene as a clear oil; 1H NMR (δ, CDCl3) 7.63 (m, 2H), 8.16(s, 1H), 8.23 (m, 1H); 19F NMR (δ, CDCl3) -79.8 (1F), -81.6 (3F), -85.2 (AB quartet with fine structure, 2F); -87.3 (2F), -130.4 (2F). Anal. Calcd for C11H4ClF10NO4 : C, 30.05; H, 0.92; N, 3.12; Cl, 8.06; F, 43.22. Found: C, 29.79; H, 0.82; N, 3.54; Cl, 8.39; F, 40.19.

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