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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence