2,2,2-Trifluoroethanol → 1-Bromo-4-chloro-5-(4-ethylbenzyl)-2-(2-(2,2,2-trifluoroethoxy)ethoxy)benzene

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Reaction Steps

To a solution of 2-(2-bromo-5-chloro-4-(4-ethylbenzyl)phenoxy)ethanol (AU) (0.53 g, 1.4 mmol) in anhydrous CH2Cl2 (4 mL), was added 2,2,2-trifluoroethanol (0.43 g, 4.3 mmol) and triphenylphosphine polystyrene resin (0.57 g, 2.2 mmol). The resulting mixture was stirred overnight at room temperature, after which it was heated for 2 h at 45° C. The mixture was absorbed onto Celite and purified using silica gel column chromatography eluting with a gradient of EtOAc in hexanes to give intermediate BR. 1H-NMR (CDCl3, 300 MHz) δ 7.36 (s, 1H), 7.14 (m, 4H), 6.94 (s, 1H), 4.17-4.01 (m, 8H), 2.67 (q, J=7.5 Hz, 2H), 1.27 (t, J=7.5 Hz, 3H).

Provenance & Evidence