تفاعل #90089

معادلة التفاعل

hydrochloric acid

methanesulfonic acid

2-(3-bromo-4-methoxy-phenyl)-2-methyl-propionitrile

bromoethyl acetate

→

title compound

المردود 72.0%

4-(3-Bromo-4-methoxy-phenyl)-4-methyl-3-oxo-pentanoic acid ethyl ester

المردود 72.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe mixture was further stirred for 30 min
3. 3
   workup.STIRRINGstirred at room temperature overnight
4. 4
   استخلاصAfter extraction with ethyl acetate
5. 5
   غسيلthe organic layer was washed with brine
6. 6
   تجفيفdried over sodium sulfate
7. 7
   أخرىThe drying agent was removed by filtration
8. 8
   أخرىthe residues obtained
9. 9
   تركيزafter concentration under reduced pressure
10. 10
    أخرىwere purified by silica gel column chromatography (ethyl acetate/hexane)

الإجراء التجريبي

To the THF suspension of zinc (5.72 g, 2 eq.), methanesulfonic acid (25.6 μl, 0.01 eq.) was added, and then stirred at 80° C. for 10 min. Then, the THF solution of 2-(3-bromo-4-methoxy-phenyl)-2-methyl-propionitrile (10 g, 39.35 mmol) was added, followed by addition of bromoethyl acetate (11.07 ml, 1.6 eq.) over 1 hr. The mixture was further stirred for 30 min. To the reaction solution, 4 M hydrochloric acid was added, and stirred at room temperature overnight. After extraction with ethyl acetate, the organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (orange oily substance, 9.74 g, 72%).

المصدر