Pyridine → 2-(2-BROMO-5-METHOXYPHENYL)ETHANOL

To a stirred mixture of 3-methoxyphenethyl alcohol (1.18 g, 7.8 mmol) and pyridine (0.75 ml, 9.3 mmol) in dry dichloromethane (10 ml) was added bromine (0.47 ml, 18.0 mmol) dropwise under nitrogen at 0° C. The orange solution was stirred at room temperature for 4 hours (hr). The reaction mixture was quenched by the addition of 10% sodium bisulfite aqueous solution., and extracted with dichloromethane. The organic extracts were washed with brine, dried over magnesium sulfate, and concentrated to give crude products, which were purified by silica-gel column chromatography eluted with gradient of hexane and ethyl acetate (10:1, 8:1, 5:1) to give the title compound as a colorless oil (1.5 g, 83.2%). 1H-NMR (CDCl3): 7.43 (d, J=8.8 Hz, 1H), 6.83 (d, J=3.3 Hz, 1H), 6.67 (dd, J=8,8, 3.3 Hz, 1H), 3.91-3.81 (m, 2H), 3.78 (s, 3H), 2.99 (t, J=6.6 Hz, 2H).

1. customThe reaction mixture was quenched by the addition of 10% sodium bisulfite aqueous solution
2. extraction, and extracted with dichloromethane
3. washThe organic extracts were washed with brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated
6. customto give crude products, which
7. customwere purified by silica-gel column chromatography
8. washeluted with gradient of hexane and ethyl acetate (10:1, 8:1, 5:1)

ORD record

ord-7b04892886ad4946b33bf4feef0143fa

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06239147B1