Ammonium Chloride → 4-((5-Chloro-furan-2-yl)-hydroxy-methyl)-benzonitrile

Temperatur

0 °C

To a mixture of 4-iodobenzonitrile (3.0 g, 13 mmol) and tetrahydrofuran (40 mL) was added dropwise isopropyl magnesium chloride (1-2 M diethyl ether solution, 11 mL, 11-22 mmol) at −78° C., which was stirred for 1 hour at 0° C. The reaction mixture was cooled to −78° C., 5-chloro-2-furaldehyde (2.2 g, 17 mmol) was added at that temperature, and the temperature was gradually raised to 0° C. Following 30 minutes of stirring at 0° C., saturated aqueous ammonium chloride solution, water and ethyl acetate were added to extract the reaction mixture. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. Ethyl acetate was added to the residue, which was then filtered with NH silica gel. The filtrate was concentrated under a reduced pressure to obtain the title compound (3.2 g) as a crude product. This compound was used in the subsequent reaction without further purification.

1. temperatureThe reaction mixture was cooled to −78° C.
2. temperaturethe temperature was gradually raised to 0° C
3. waitFollowing 30 minutes
4. stirringof stirring at 0° C.
5. extractionto extract the reaction mixture
6. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride
7. customthe solvent was evaporated under a reduced pressure
8. additionEthyl acetate was added to the residue, which
9. filtrationwas then filtered with NH silica gel
10. concentrationThe filtrate was concentrated under a reduced pressure

ORD-Eintrag

ord-0490ca2bc323481e8b619c953da2965f

Quelldatensatz

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08153662B2