Toluene → (3-Chloro-4-iodo-5-methoxyphenyl)methanol

Temperature

-78 °C

To a mixture of ethyl 3-chloro-4-iodo-5-methoxybenzoate (15.6 g, 45.8 mmol) and toluene (150 mL), was added diisobutyl aluminum hydride (1.01M toluene solution: 95.2 mL, 96.2 mmol) while stirring at −78° C., and the mixture was stirred while warming to −30° C. for three hours. To the mixture, an aqueous solution (400 mL) of Rochelle salt (potassium sodium (+)-tartrate tetrahydrate) (77.6 g, 275 mmol) was added, the mixture was stirred at room temperature for five hours, followed by addition of ethyl acetate. 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 (13.7 g, 45.8 mmol).

1. stirringthe mixture was stirred
2. temperaturewhile warming to −30° C. for three hours
3. stirringthe mixture was stirred at room temperature for five hours
4. stirringAfter thoroughly shaking the mixture
5. customthe organic layer was separated
6. washthe organic layer was washed with brine
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationThe mixture was filtered
9. distillationthe solvent in the filtrate was distilled off under reduced pressure

ORD record

ord-1bbe67e71f234738a46e25bab67a2b00

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530504B2