1-(Bromomethyl)naphthalene

Off-white powder

General procedure: Ethyl α, α-dibromoacetoacetate 2a (0.41 mmol, 1.2 equiv), alcohols 1a-1s (0.34 mmol, 1.0 equiv) and Ph3P (0.68 mmol, 2.0 equiv) were added under ambient temperature to 3 mL of DCE in air. After stirred at room temperature for appropriate time (monitored by TLC), the reaction was quenched by addition of H2O (3 mL) and then extracted with ethyl acetate (3×3 mL). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography on silica gel with petroleum ether or mixture of petroleum ether and ethyl acetate as eluent to afford the corresponding products 3a-3s.4-methyl-7-(naphthalene-1-ylmethoxy)-2H-chromen-2-one (4Z) l\-Ε.-\ΔΛ-SUQQΛP0C. PBrGeneral procedure: a solution of the arene (2.0 mmol) and TBCA (0.25 g, 0.68 mmol) in EtOAc (20 mL) was refluxed for 6 h with stirring. At the end of the reaction, the precipitated cyanuric acid was then separated by filtration and the filtrate was evaporated to dryness under reduced pressure. The residue was passed through a short chromatographic column (SiO2, eluted with 15:1 hexane–ethyl acetate) to give the purified products.

Molecular Weight:221.09
XLogP3:3.8
Rotatable Bond Count:1
Exact Mass:219.98876
Monoisotopic Mass:219.98876
Heavy Atom Count:12
Complexity:144
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes