反応 #42617

反応方程式

Methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate

copper (I) cyanide

→

desired product

methyl 3-cyano-5-[(dipropylamino)carbonyl]benzoate

溶媒

N-methylpyrrolidinone

反応条件

後処理

1. 1
   温度was cooled
2. 2
   その他partitioned between ethyl acetate and aq. HCl (1N)
3. 3
   乾燥The organic layer was dried (magnesium sulfate)
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他the residue was chromatographed on silica gel

実験手順

Methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (Preparation 3) (0.15 g), copper (I) cyanide, and N-methylpyrrolidinone (1 mL) was heated at 150° C. overnight, at which time the mixture was cooled and partitioned between ethyl acetate and aq. HCl (1N). The organic layer was dried (magnesium sulfate), concentrated under reduced pressure, and the residue was chromatographed on silica gel using ethyl acetate-hexane (20/80) to give 0.066 g of the desired product. ms (m+H) 289.2. See also preparation 7 for the preparation of the acid.

出典