Boron tribromide → 3-Bromo-5-methoxyphenol

Temperature

-78 °C

1-bromo-3,5-dimethoxybenzene (3.0 g, 13.8 mmol) was dissolved in dichloromethane (45 mL) and the solution was cooled to −78° C. Boron tribromide (1M in dichloromethane, 41 mL, 41 mmol) was added and the solution was warmed gradually to room temperature over 18 hours. After cooling to −78° C., the reaction was quenched with water (100 mL). The organics were separated and washed with sodium thiosulphate solution then water, then dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with pentane:ethyl acetate 100:0 to 80:20, to afford the title compound in 16% yield (470 mg).

1. temperaturethe solution was warmed gradually to room temperature over 18 hours
2. temperatureAfter cooling to −78° C.
3. customthe reaction was quenched with water (100 mL)
4. customThe organics were separated
5. washwashed with sodium thiosulphate solution
6. dry with materialwater, then dried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue was purified by column chromatography on silica gel
9. washeluting with pentane:ethyl acetate 100:0 to 80:20

ORD record

ord-f1853c645e7f4900bd86b98bc931d9dd

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268881B2