Reaction #1694981

Reaction equation

copper cyanide

caesium fluoride

1-[4-pentylbicyclo(2.2.2)octyl]-2-(4-cyano-3-nitrophenyl)ethane

1-[4-pentylbicyclo(2.2.2)octyl]-2-(4-bromophenyl)-ethane

→

1-[4-pentylbicyclo(2.2.2)octyl]-2-(4-cyano-3-fluorophenyl)-ethane

Solvents

N-methylpyrrolidone

Conditions

Workup

1. 1
   Othersubsequently purifying the product by chromatography) and 25 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone
2. 2
   Temperaturethe mixture is heated at 120oC for 5 hours
3. 3
   Extractionafter extraction

Procedure

7.6 g of caesium fluoride are added to a mixture of 3.55 g of 1-[4-pentylbicyclo(2.2.2)octyl]-2-(4-cyano-3-nitrophenyl)ethane (obtainable by nitrating 1-[4-pentylbicyclo(2.2.2)octyl]-2-(4-bromophenyl)-ethane, reacting the product with copper cyanide in N-methylpyrrolidone and subsequently purifying the product by chromatography) and 25 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, and the mixture is heated at 120oC for 5 hours. Adding water and working up after extraction gives 1-[4-pentylbicyclo(2.2.2)octyl]-2-(4-cyano-3-fluorophenyl)-ethane.

Source