1-(trifluoromethoxy)-2-(2-(trifluoromethoxy)ethoxy)ethane synthesis

Yield:329710-73-8 82%

Reaction Conditions:

with 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione;pyridine hydrogenfluoride in dichloromethane at 20; for 1.5 h;Acidic conditions;

Steps:

195.iia (iia)

HF-PYRIDINE complex (42 ml) followed by dithiocarbonic acid S-methyl ester 0- [2- (2-methylsulfanylthiocarboxyoxy-ethoxy)-ethyl] ester (8.4g, 29. 3mmol), was added to a cold (-78°C) solution of 1, 3-DIBROMO-5, 5-dimethylhydantoin (51.18g, 179 mmol) in dichloromethane (300 ml). The reaction was warmed to ambient temperature and stirred for 1.5 hours, then poured into cold aqueous saturated sodium chloride. The layers were separated, and the aqueous layer extracted with dichloromethane. The combined organic extracts were washed with cold 37% aqueous NAHS03 and cold aqueous saturated sodium chloride then dried over MGS04, filtered, and concentrated in vacuo at ambient temperature. The residue was purified by bulb to bulb distillation under mild vacuum at 120°C and trapped AT-78°C to yield (5.81g, 82%) of 1-TRIFLUOROMETHOXY-2- (2- TRIFLUOROMETHOXY-ETHOXY) -ETHANE : LH NMR (400 MHZ, CDC13) : 8 = 4.0 (4H, M), 3.70 (4H, m).

References:

WO2004/52858,2004,A2 Location in patent:Page 163