Synthesis
The general procedure for the synthesis of 4-bromomethylbenzyl alcohol from methyl 4-bromomethylbenzoate was as follows: under nitrogen protection, methyl 4-bromomethylbenzoate (5.73 g, 25 mmol) was dissolved in anhydrous CH2Cl2 (150 mL), stirred and cooled to -78 °C. DIBAL-H solution (82.5 mL, 1.0 M THF solution) was added slowly and dropwise. The -78 °C reaction temperature was maintained and stirring was continued for 1.5 hours. Subsequently, the reaction mixture was slowly warmed to 0 °C and the reaction was quenched with H2O. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2 x 100 mL). The organic extracts were combined, dried with MgSO4 and the solvent was evaporated under reduced pressure to afford the target product 4-bromomethylbenzyl alcohol (5.0 g, 100% yield) as a white solid. The product was characterized by 1H NMR (CDCl3): δ1.84 (br, 1H), 4.49 (s, 2H), 4.67 (s, 2H), 7.33 (d, 2H, J=8.2Hz), 7.38 (d, 2H, J=8.2Hz).
References
[1] Patent: US6506770, 2003, B1
[2] Patent: US6872714, 2005, B1
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1250 - 1260
[4] European Journal of Medicinal Chemistry, 2015, vol. 104, p. 127 - 138
[5] Journal of Labelled Compounds and Radiopharmaceuticals, 2017, vol. 60, # 10, p. 466 - 480
