Synthesis
General procedure for the synthesis of 4-tert-butylbenzyl bromide from 4-tert-butyltoluene: Referring to Example 19 Preparation of N-(4-tert-butylbenzyl)methanamine (Alternative method), 4-tert-butyltoluene (14.8 g, 0.10 mol) was dissolved in carbon tetrachloride, and N-bromosuccinimide (17.8 g, 0.10 mol) and benzoyl peroxide (200 mg) were added . The reaction mixture was refluxed for 2 h and subsequently cooled to room temperature. The insoluble material was removed by filtration and the filtrate was washed with carbon tetrachloride. The filtrate was concentrated under reduced pressure and the resulting residue was dissolved in hexane and dried with magnesium sulfate. Finally, the solvent was evaporated under reduced pressure to give 22.7 g of 4-tert-butylbenzyl bromide (yield: 100%).
References
[1] Patent: US6586633, 2003, B1
[2] Patent: CN105315127, 2016, A. Location in patent: Paragraph 0044-0050
[3] Tetrahedron Letters, 2009, vol. 50, # 16, p. 1861 - 1865
[4] Synthesis, 2009, # 11, p. 1807 - 1810
[5] Synthetic Communications, 2010, vol. 40, # 7, p. 998 - 1003
