Hydrochloric Acid → 3-Isopropyl-4-methoxyphenylacetonitrile

Temperature

-78 °C

An isopropylmagnesium bromide-0.63M tetrahydrofuran solution (3.2 ml, 2.0 mmol) was added dropwise to a solution of zinc bromide (473 mg, 2.1 mmol) in tetrahydrofuran (2 ml) under ice-cooling. After the mixture was stirred for 15 minutes, the reaction mixture was cooled to −78° C. After 3-bromo-4-methoxybenzyl cyanide (226 mg, 1.0 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane adduct (32 mg, 0.04 mmol) were added to the mixture at −78° C., the temperature of the reaction mixture was raised to room temperature and the mixture was further stirred for 5 hours. 1N Hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was subjected to silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=8/1-6/1) to give crude (3-isopropyl-4-methoxyphenyl)acetonitrile (158 mg).

1. temperaturecooling
2. temperaturethe temperature of the reaction mixture was raised to room temperature
3. stirringthe mixture was further stirred for 5 hours
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was successively washed with water
6. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
7. customThe residue obtained
8. customby removing the solvent under reduced pressure
9. washwas subjected to silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=8/1-6/1)

ORD record

ord-5878e995c9cd44a3ac082cdb4fe373ac

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923573B2