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 1 hour. Water was slowly added to the mixture while cooling on ice, and then the solvent in the mixture was distilled off under reduced pressure. Water and ethyl acetate were added to the residue. 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 then filtered, and 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 1 hour
4. temperaturewhile cooling on ice
5. distillationthe solvent in the mixture was distilled off under reduced pressure
6. additionWater and ethyl acetate were added to the residue
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 then filtered
11. distillationthe solvent in the filtrate was distilled off under reduced pressure

ORD record

ord-25a4b09b21db465b94da0c93da96f0ca

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431603B2