Synthesis
The general procedure for the synthesis of 2-bromo-5-hydroxymethyl anisole from m-methoxybenzyl alcohol was as follows: to a solution of 3-methoxybenzyl alcohol (20.0 g, 145 mmol) in tetrahydrofuran (THF, 400 mL) was added N-bromosuccinimide (NBS, 26 g, 146 mmol). The reaction mixture was stirred at room temperature for 8 hours. After the reaction was completed, ether (500 mL) was added to dilute and the mixture was washed with deionized water (3 x 100 mL). The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford 2-bromo-5-hydroxymethyl anisole (31.2 g, 99% yield), and the product was used directly in the next reaction without further purification.
References
[1] Patent: US9725406, 2017, B1. Location in patent: Page/Page column 7-8
[2] Tetrahedron, 2005, vol. 61, # 49, p. 11692 - 11696
[3] Patent: US2018/208604, 2018, A1. Location in patent: Paragraph 0201-0203
[4] Patent: US2010/4159, 2010, A1. Location in patent: Page/Page column 59; 64
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1010 - 1014
