Synthesis
At -20 °C, tert-butyl (3-(hydroxymethyl)phenylcarbamate (120 g, 484 mmol) was dissolved in tetrahydrofuran (50 mL) and triphenylphosphine (254 g, 967 mmol) and N-bromosuccinimide (103 g, 580 mmol) were added sequentially. The reaction mixture was stirred at this temperature for 3 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being petroleum ether: ethyl acetate (100:1, v/v) to afford tert-butyl 3-(bromomethyl)phenylcarbamate (125 g, 437 mmol, 90% yield) as a white solid. It was analyzed by liquid chromatography-mass spectrometry (LCMS, Method 1, Table 7) with a retention time (R t) of 2.10 min; mass spectrometry (MS) showed m/z = 230,232 [M-t-Bu + H+].
References
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[2] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 1, p. 73 - 93
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[4] Patent: US2008/21032, 2008, A1. Location in patent: Page/Page column 56
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