An Efficient K₂CO₃-Promoted Synthesis of 1-Bromo-2-aryloxyethane Derivatives and Evaluation of Larval Mortality against Aedes aegypti

Abstract

The influences of reaction parameters on the etherification of phenols to obtain 1-bromo-2-aryloxyethane derivatives were evaluated. The compounds were prepared by direct etherification of phenols with 1,2-dibromoethane using anhydrous K 2 CO 3 and acetonitrile as solvent reaction, at 80 ∘ C, in a reaction time of 6 h. Under these conditions, excellent yields (71%-94%) were obtained, with low yields of secondary products. The anhydrous K 2 CO 3 was recycled by simple filtration, dried in vacuum, and reused. The compounds were characterized by conventional spectral data (MS and NMR). Larvicidal activity results showed a 100% larval mortality after 24-hour exposure to the compound 1-(2-bromoethoxy)-2-phenylbenzene.

Subnanomolar Affinity and Selective Antagonism at α7 Nicotinic Receptor by Combined Modifications of 2-Triethylammonium Ethyl Ether of 4-Stilbenol (MG624)

“…The crude was purified by silica gel flash column chromatography (cyclohexane/EtOAc 95:5) providing the desired product 35 as a white powder in a 46% yield. R f = 0.57 (cyclohexane/EtOAc 9:1) mp = 112 °C (coherent with the literature 15 ).…”

“…Obtained from (E)-2-(4-(4bromostyryl)phenoxy)-N,N-diethylethan-1-amine 54 (315 mg, 0.84 mmol, 1 equiv) and iodoethane (2 equiv) in THF (5 mL), according to Method B at reflux temperature, overnight. Upon cooling at room temperature, the reaction mixture was diluted with diethyl ether and (15). Obtained from 62 (47 mg, 0.112 mmol, 1 equiv) and triethylamine in toluene (1:1 v/v, 5 mL) at reflux for 16 h. Upon cooling to room temperature, diethyl ether was added and the solid was collected by filtration to give 15 as an offwhite solid in a 32% yield.…”

Synthesis, solid state self-assembly driven by antiparallel π⋯π stacking and {⋯H–C–C–F}2dimer synthons, andin vitroacetyl cholinesterase inhibition activity of phenoxy pendant isatins

“…: 57–58 °C (lit. 56–58 °C); 58 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) 7.38–7.43 (2H, m, aromatic), 6.79–6.84 (2H, m, aromatic), 4.26 (2H, t, 3 J = 6.3 Hz, H-2), 3.64 (2H, t, 3 J = 6.0 Hz, H-1). 13 C NMR (75 MHz, CDCl 3 ) δ (ppm): 28.95 (C-1), 68.06 (C-2), 113.66 (C-3) 116.56 (C-4a, 4a′), 132.43 (C-5a, 5a′), 157.21 (C-6).…”

“…The synthesis of phenoxy pendant isatins PI1-12 was initiated with the preparation of 1-(2-bromoethoxy)-4-substituted benzenes B1-4 (Scheme 1). The treatment of substituted phenols A1-4 with large excess of 1,2-dibromoethane at 50 C in CH 3 CN : DMF (9 : 1) mixture provided desired intermediates B1-4 [58][59][60] in 62-70% isolated yields. The intermediates B1-4 were nally reacted with isatin, 5-chloroisatin and 5-bromoisatin in DMF solvent in the presence of K 2 CO 3 as base at 60 C to furnish phenoxy pendant isatins PI1-12 in excellent (83-85%) yields (Scheme 1).…”

“…58 1 H NMR (300 MHz, CDCl 3 ): d (ppm) 7.38-7.43 (2H, m, aromatic), 6.79-6.84 (2H, m, aromatic), 4.26 (2H, t, 3 J ¼ 6.3 Hz, H-2), 3.64 (2H, t, 3 J ¼ 6.0 Hz, H-1) 13. C NMR (75 MHz, CDCl 3 ) d (ppm): 28.95 (C-1), 68.06 (C-2), 113.66 (C-3) 116.56 (C-4a, 4a 0 ), 132.43 (C-5a, 5a 0 ), 157.21 (C-6).…”