Hydrochloric Acid → 2-(4-Bromo-2-methylphenyl)ethanol

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A solution of 30A (1.5 g, 7.6 mmol) in 0.5 M 9-BBN in THF (40 mL, 20 mmol) was heated at 120° C. in a sealed tube for 15 min in a microwave. The mixture was cooled to 0° C. in a 250 mL Erlenmeyer flask. NaOH (1.0 M, 40 mL) then H2O2 (30%, 40 mL) were added slowly dropwise while maintaining the internal temperature below 30° C. HCl (1.0 M, 40 mL) was added and the mixture was extracted with Et2O (2×100 mL). The organics were combined, washed with NaHCO3, brine, dried over Na2SO4 and concentrated in vacuo. The crude oil was purified by flash chromatography (0% to 50% hexanes in EtOAc) to yield 30B (1.05 g, 64%) as a clear oil. 1H NMR (400 MHz, MeOD) δ ppm 2.30 (s, 3 H) 2.80 (t, J=7.20 Hz, 2 H) 3.69 (t, J=7.07 Hz, 2 H) 7.06 (d, J=8.08 Hz, 1 H) 7.23 (dd, J=8.21, 1.89 Hz, 1 H) 7.28-7.31 (m, 1 H).

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