Synthesis
General procedure for the synthesis of 1-bromo-4-bromomethylnaphthalene from 1-bromo-4-methylnaphthalene: 3.3 g (10.2 mmol, 1.5 eq.) of 4-bromo-1-methylnaphthalene was accurately weighed and added to 30 mL of ethyl acetate, followed by tetrabutylammonium bromide. The reaction mixture was stirred at reflux for 9 hours at 70 °C. The reaction progress was monitored by thin layer chromatography (TLC) and the reaction was terminated after confirming complete conversion of the feedstock. The reaction mixture was filtered and the filter cake was collected. The filter cake was stirred with 30 mL of ethyl acetate for 2 h at room temperature and filtered again to give 1.60 g of 1-bromo-4-(bromomethyl)naphthalene as a light yellow solid in 77.43% yield.
References
[1] European Journal of Organic Chemistry, 2006, # 10, p. 2329 - 2335
[2] Journal of Organic Chemistry, 1999, vol. 64, # 4, p. 1387 - 1390
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[4] Patent: CN105906530, 2016, A. Location in patent: Paragraph 0091; 0092; 0093; 0094; 0095
[5] Organic Letters, 2008, vol. 10, # 14, p. 3105 - 3108
