Methyl iodide → 2-(2,3-Difluorophenyl)propanenitrile

温度

-78 °C

A solution of 1.586 g (16 mmol) diisopropylamine in 25 ml tetrahydrofuran was cooled with sodium chloride/ice to −10° C. A solution of 9 ml (14 mmol) 1.6 M butyl lithium in hexanes was added drop-wise. After stirring for 10 min the resulting LDA solution was cooled to −78° C. and a solution of 2.00 g (13 mmol) 2,3-difluorophenyl-acetonitrile in 5 ml tetrahydrofuran slowly added. The reaction mixture was stirred at −78° C. for 40 min, then 2.22 g (16 mmol) methyl iodide were added and the cooling bath was removed after 5 min. The mixture was stirred for 2.5 h at room temperature, and then aqueous ammonium chloride solution was added. The mixture was extracted twice with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and evaporated. The residue was purified using column chromatography (SiO2, heptanes/ethyl acetate 9:1) to yield 1.12 g of rac-2-(2,3-difluoro-phenyl)-propionitrile as a light yellow liquid; MS (EI): 167.1 (M+.), 152.1 (((M-CH3)+.), 100%).

1. customthe cooling bath was removed after 5 min
2. stirringThe mixture was stirred for 2.5 h at room temperature
3. additionaqueous ammonium chloride solution was added
4. extractionThe mixture was extracted twice with ethyl acetate
5. dry with materialThe combined organic layers were dried over MgSO4
6. filtrationfiltered
7. customevaporated
8. customThe residue was purified

ORDレコード

ord-9518038270fa409dbd21d8c147bb3eb4

出典データセット

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07875645B2