Synthesis
The general procedure for the synthesis of 1-bromomethylnaphthalene from 1-naphthalenemethanol: Ethyl α,α-diacetoacetate (0.41 mmol, 1.2 eq.), 1-naphthalenemethanol (0.34 mmol, 1.0 eq.), and triphenylphosphine (0.68 mmol, 2.0 eq.) were added to 3 mL of dichloroethane (DCE) at room temperature and the reaction took place in air. The progress of the reaction was monitored by thin layer chromatography (TLC) during the reaction. Upon completion of the reaction, the reaction was quenched by the addition of 3 mL of water, followed by extraction with ethyl acetate (3 x 3 mL). The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography, and the eluent was petroleum ether or a mixed solvent of petroleum ether and ethyl acetate, and the target product 1-bromomethyl naphthalene was finally obtained.
References
[1] Synthetic Communications, 2010, vol. 40, # 11, p. 1646 - 1649
[2] Organic Letters, 2003, vol. 5, # 8, p. 1167 - 1169
[3] Tetrahedron Letters, 2014, vol. 55, # 1, p. 90 - 93
[4] Canadian Journal of Chemistry, 1981, vol. 59, p. 2629 - 2641
[5] Tetrahedron, 2003, vol. 59, # 52, p. 10453 - 10463
