Hydrochloric Acid → 3-Bromo-5-methoxyphenol

Temperature

100 °C

Commercially available 1-bromo-3,5-dimethoxybenzene (18.74 g, 86.3 mmol) was dissolved in 1-methyl-2-pyrrolidone (100 mL), and sodium thiomethoxide (6.74 g, 96.2 mmol) was added, followed by stirring at 100° C. for 3 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, 1N hydrochloric acid (200 mL) was added, and extraction was carried out with diethyl ether (500 mL). The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=20%-25%) to afford the desired compound (15.03 g, yield 86%) as a white solid.

1. temperatureThe reaction solution was cooled to room temperature
2. extractionextraction
3. washThe organic layer was washed with saturated brine
4. dry with materialsubsequently dried over sodium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customthe resulting residue was purified
7. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=20%-25%)

ORD record

ord-0996f2e8220045f8be9121223c60d2c1

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415359B2