4-(2,2,2-TRIFLUOROETHOXY)NITROBENZENE synthesis

12synthesis methods

Product Name:4-(2,2,2-TRIFLUOROETHOXY)NITROBENZENE
CAS Number:62149-35-3
Molecular formula:C8H6F3NO3
Molecular Weight:221.13

75-89-8
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350-46-9 Synthesis

350-46-9
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62149-35-3
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Yield:62149-35-3 98%

Reaction Conditions:

Stage #1: 2,2,2-trifluoroethanolwith sodium hydride in tetrahydrofuran at 0 - 20; for 1 h;
Stage #2: 4-Fluoronitrobenzene in tetrahydrofuran at 20; for 3 h;

Steps:

68 4-(2,2,2-Trifluoroethoxy)nitrobenzene

To a solution of 2,2,2-trifluoroethanol (26.49 g, 0.26 mol) in THF (300 mL) was added sodium hydride (in oil, 65%, 10.27 g, 0.28 mol) under ice-cooling, and the mixture was stirred for 1 hr at room temperature. To this mixture was added p-fluoronitrobenzene (37.36 g, 0.26 mol), and the mixture was stirred for 3 hr at room temperature. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (56.13 g, yield 98%) as a yellow amorphous solid. ¹H-NMR (300MHz, CDCl₃) δ:4.46 (2H, q, J = 7.8 Hz), 7.04 (2H, d, J = 9.2 Hz), 8.25(2H, d, J = 9.2 Hz).

References:

EP1810677,2007,A1 Location in patent:Page/Page column 61

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