Reaktion #565259

Reaktionsgleichung

potassium pentafluoropropionate

6-methoxy-5-bromo-1-cyanonaphthalene

toluene

N,N-dimethylformamide

→

6-methoxy-5-pentafluoroethyl-1-cyanonaphthalene

Lösungsmittel

toluene water

methylene chloride

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   FiltrationThe two phases were filtered
3. 3
   Sonstigeafter which the organic layer was separated
4. 4
   Waschenwashed with brine
5. 5
   Einengenconcentrated in vacuo

Vorschrift

A suitable reaction vessel was charged with 8.1 g of 6-methoxy-5-bromo-1-cyanonaphthalene, 11.8 g of CuI, 35 ml of toluene, and 55 ml of N,N-dimethylformamide. The reaction mixture was heated to 165° C. with concurrent azeotropic removal of toluene/water (25 ml) and then maintained at 155° C. when 11.8 g of potassium pentafluoropropionate was added. The reaction was monitored by VPC. After five hours no starting material was detected and the reaction mixture was poured into 150 ml of water and 125 ml of methylene chloride. The two phases were filtered, after which the organic layer was separated, washed with brine, and concentrated in vacuo to provide a crude 6-methoxy-5-pentafluoroethyl-1-cyanonaphthalene (6-MPCN) having a purity of greater than 95%.

Quelle