2-(Bromomethyl)benzyl alcohol, 95%

Synthesis

To 48% hydrobromic acid (15.0 mL) was added 1,2-benzenedimethanol (4.0 g, 29.0 mmol), and the reaction mixture was stirred for 2 h at room temperature. After the reaction was completed, 1N NaOH aqueous solution was added to neutralize to pH 7. The reaction mixture was diluted with ethyl acetate (200 mL), washed sequentially with saturated NaHCO3 solution (20 mL) and brine (20 mL), and the organic phase was dried over anhydrous Na2SO4. The solvent was removed by concentration under reduced pressure and the crude product was purified by silica gel column chromatography (Combi Flash Rf apparatus, ethyl acetate/hexane solvent system, 0-30% gradient elution) to afford 2.6 g (45% yield) of the target compound S14 as a white solid.1H NMR (500 MHz, CDCl3) δ: 7.30-7.45 (m, 4H), 4.85 (s, 2H), 4.64 (s, 2H), 1.81 (br s, 1H).

References

[1] Journal of the American Chemical Society, 2010, vol. 132, # 49, p. 17366 - 17369
[2] Journal of the American Chemical Society, 1980, vol. 102, p. 4193
[3] Synthesis, 1982, # 12, p. 1014 - 1015
[4] Patent: WO2015/69932, 2015, A1. Location in patent: Page/Page column 90; 91
[5] Patent: WO2015/188197, 2015, A2. Location in patent: Page/Page column 78