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

Temperature

0 °C

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).

1. temperaturewhile maintaining the internal temperature below 30° C
2. extractionthe mixture was extracted with Et2O (2×100 mL)
3. washwashed with NaHCO3, brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customThe crude oil was purified by flash chromatography (0% to 50% hexanes in EtOAc)

ORD record

ord-ae732271570e4603856cb0bbdded2ef3

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592331B2