Hydrochloric Acid → HCID 13515581, compound

Participants

Reaction Steps

According to the procedure of J. T. Gupton et al, Can. J. Chem. 63, 3037 (1985), a suspension of hexane-washed sodium hydride (8.4 g, 0.21 mol) in DMF (250 mL) was added to 2,2,2-trifluoroethanol (22.1 mL, 0.3 mol) dropwise in 200 mL of DMF at room temperature over 60 minutes (excessive frothing occurs if added too fast). After stirring an additional 30 minutes 2,3-dichloronitrobenzene (38 g, 0.20 mol) was added in one portion. The resulting mixture was stirred at room temperature for 2 hours. The reaction was then poured into 1N HCl (500 mL) and extracted with Et2O (2×500 mL). The combined Et2O layers were washed first with water (200 mL) and finally with saturated brine (200 mL). After drying (MgSO4), the ether was concentrated to yield 47 g (90% based on dichloronitrobenzene) of 3-chloro-2-(2,2,2-trifluoroethoxy)nitrobenzene as a yellow liquid (b.p. 85° C./0.3 mmHg), which was used without further purification.

Provenance & Evidence