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 diisobutylaluminum hydride (1.01 M solution in toluene: 95.2 mL, 96.2 mmol) while stirring at −78° C., and stirring was continued for 3 hours while raising the temperature to −30° C. After then adding a solution of Rochelle salt (sodium potassium (+)-tartrate tetrahydrate) (77.6 g, 275 mmol) in water (400 mL) to the mixture, stirring was continued for 5 hours at room temperature and ethyl acetate was 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 then filtered, and the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (13.7 g, 45.8 mmol).

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

ORD record

ord-69aa0cca2d3e465982fe014a35b84a4c

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431603B2