Benzonitrile, 4-bromo- → HCID 21270874, compound

Participants

Reaction Steps

A mixture of 37.8 g of 2-(3-nitro-4-bromophenyl)-5-n-heptylpyrimidine (obtainable by nitration of 4-bromobenzonitrile, converting the 3-nitro-4-bromobenzonitrile into the corresponding amidine hydrochloride and heating the latter together with n-heptylmalondialdehydtetramethylacetale), 18 g of Cu-(I)-cyanide and 100 ml of 1,3-dimethyltetrahydro-2(1H)pyrimidinon (DMPU) is heated at 150° for 3 hours. After cooling the mixture is filtered, the filtrate and the residue are extracted with methylene chloride and the organic phase is evaporated. 2-(3-Nitro-4-cyanophenyl)-5-n-heptylpyrimidine (F. 73°) is obtained by purification by chromatography. The obtained material is heated together with 33.4 g of CsF in 120 ml of DMPU at 110° for 4 hours. After cooling the mixture is poured onto 600 ml of ice water. After extraction with methylene chloride and purification by chromatography 2-(3-fluoro-4-cyanophenyl)-5-n-heptylpyrimidine (m.p. 43°, clp. 0°, Δε=-37) is obtained

Provenance & Evidence