m-Chloroperbenzoic acid → 4-Chloro-2-(ethylsulfinyl)-6-methyl-benzonitrile

To a stirred solution of 4-chloro-2-ethylsulfanyl-6-methyl-benzonitrile (synthesized according to the method described in section a) of example 2) (1.00 g, 4.73 mmol) in dichloromethane (20 ml) is added meta-chloroperoxybenzoic acid (0.58 g, 2.36 mmol, 70% suspension) portion wise at 0° C. The resulting mixture is stirred at 0° C. for 15 min. The white suspension is dissolved in ethyl acetate (25 ml) and the solvent is distilled off. The residue is again diluted with ethyl acetate (15 ml) and washed with 10% sodium sulphite solution (3×15 ml), saturated sodium hydrogen sulfate solution (3×15 ml), brine (15 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 8% ethyl acetate/hexane) to yield 4-chloro-2-(ethylsulfinyl)-6-methyl-benzonitrile (0.4 g, 1.76 mmol, 37%).

1. distillationthe solvent is distilled off
2. additionThe residue is again diluted with ethyl acetate (15 ml)
3. washwashed with 10% sodium sulphite solution (3×15 ml), saturated sodium hydrogen sulfate solution (3×15 ml), brine (15 ml)
4. dry with materialdried over anhydrous sodium sulfate
5. customevaporated
6. customto get the crude product, which
7. customis purified by column chromatography (silica gel, 8% ethyl acetate/hexane)

ORDレコード

ord-11c2f3c9e40f47c48acc4e2e06d6f468

出典データセット

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09108936B2