Tetrahydrofuran → (4-Bromo-3,5-dimethoxyphenyl)methanol

To a mixture of 4-bromo-3,5-dimethoxybenzoic acid (50.0 g, 192 mmol) and THF (1 L) was added borane methyl sulfide (27.1 mL, 286 mmol) while cooling on ice, and the mixture was heated to reflux for one hour. Water was gradually added to the mixture while cooling on ice, and the solvent in the mixture was then distilled off under reduced pressure. To the residue, water and ethyl acetate were added. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (47.3 g, 191 mmol).

1. temperaturewhile cooling on ice
2. temperaturethe mixture was heated
3. temperatureto reflux for one hour
4. temperaturewhile cooling on ice
5. distillationthe solvent in the mixture was then distilled off under reduced pressure
6. additionTo the residue, water and ethyl acetate were added
7. customthe organic layer was separated
8. washthe organic layer was washed with brine
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationThe mixture was filtered
11. distillationthe solvent in the filtrate was distilled off under reduced pressure

ORD record

ord-300357ba82ed451c99447bece6304569

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530504B2