Synthesis
General procedure for the synthesis of 2,4,6-trimethylbenzyl bromide from 2,4,6-trimethylbenzyl alcohol: 2,4,6-trimethylbenzyl alcohol (0.6 g, 0.6 mmol) and methylene chloride (5 mL) were added to a round bottom flask. After stirring for 10 min, oxalyl chloride or oxalyl bromide (0.6 mmol) was slowly added. The reaction mixture was stirred magnetically at room temperature until gas release essentially ceased. Subsequently, 2,4,6-trimethylbenzyl alcohol (0.5 mmol) was added and the reaction mixture was heated to reflux. The progress of the reaction was monitored by TLC and upon completion of the reaction, the mixture was cooled to room temperature and filtered. The solid on the funnel was washed with dichloromethane (3 x 10 mL), the filtrate was combined and concentrated under reduced pressure. The purity of the resulting product 2,4,6-trimethylbenzyl bromide was confirmed by 1H NMR and 13C NMR spectral analysis.
References
[1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1397 - 1405
[2] Organic Letters, 2009, vol. 11, # 2, p. 469 - 472
[3] Organic Letters, 2011, vol. 13, # 19, p. 5370 - 5373
[4] Journal of the American Chemical Society, 2018, vol. 140, # 32, p. 10099 - 10103
[5] Organic Letters, 2002, vol. 4, # 11, p. 1975 - 1977
