77532-79-7

Usage

InChI:InChI=1/C8H6FN/c1-6-2-3-8(9)4-7(6)5-10/h2-4H,1H3

Upstream product

• 452-73-3 2-chloro-4-fluorotoluene 
• 1422-53-3 2-bromo-4-fluorotoluene 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 953422-44-1 C₈H₈FNO 
• 175278-28-1 5-fluoro-2-methylbenzamide 

Downstream Products

• 198633-78-2 3-fluoro-6-methyl-2-trimethylsilylbenzonitrile 
• 1021397-33-0 N-phenyl-5-fluoro-2-methylbenzamidine 
• 77532-85-5 2-(dibromomethyl)-5-fluorobenzonitrile 
• 1425605-95-3 7-fluoro-3-phenylisoquinolin-1-amine 
• 872362-79-3 5-fluoro-N-hydroxy-2-methylbenzenecarboximidamide 
• 175278-28-1 5-fluoro-2-methylbenzamide 
• 1432519-32-8 (6R,7R)-8,8-bis(benzenesulfonyl)-13-fluoro-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-5-oxatricyclo[8.4.0.0]tetradeca-1⁽¹⁴⁾,2,10,12-tetraen-4-one 
• 1432519-35-1 (2Z)-2-({2-[2,2-bis(benzenesulfonyl)ethyl]-5-fluorophenyl}methyl)but-2-ene-1,4-diol 

Relevant academic research and scientific papers

NHC-catalyzed silylative dehydration of primary amides to nitriles at room temperature

Herein we report an abnormal N-heterocyclic carbene catalyzed dehydration of primary amides in the presence of a silane. This process bypasses the energy demanding 1,2-siloxane elimination step usually required for metal/silane catalyzed reactions. A detailed mechanistic cycle of this process has been proposed based on experimental evidence along with computational study.

A novel and convenient synthesis of benzonitriles: Electrophilic cyanation of aryl and heteroaryl bromides

N-Cyano-N-phenyl-p-methylbenzenesulfonamide has been used as a more benign electrophilic cyanation reagent for the synthesis of various benzonitriles from (hetero)aryl bromides via formation of Grignard reagents. Electronically different and sterically demanding aryl bromides including functionalized substrates and heteroaryl bromides are successfully cyanated in good to excellent yields. The efficiency of the present methodology is shown by the expeditious syntheses of interesting pharmaceutical intermediates. Notably, chemoselective monocyanation of dibromoarenes is also achieved. Copyright

Reaction of triflyl-imidazole with aldoximes: Facile synthesis of nitriles and formation of novel aldoxime-bis(N-triflyl)-imidazole adducts

The synthetic utility of N-triflylimidazole as an in situ reagent for facile, high yielding, synthesis of various aliphatic, aromatic, and heteroaromatic nitriles from the corresponding aldoximes has been demonstrated. With benzaldoximes, in the presence of certain substitutents (2-F; 2-OMe; 3-CF3; 2-Me-5-F) a different course of reaction was observed, leading instead to novel 1:1 aldoxime-bis(N-triflyl)imidazole covalent adducts, in which the aldoxime oxygen atom is bonded to the imidazole C-2 ring carbon. For these aldoximes, conversion to nitrile could be effected by reaction with Tf2O in the absence of imidazole. The molecular structure of the adduct formed from 2-methyl-5-fluoro-benzaldoxime was confirmed by X-ray analysis. Plausible mechanisms for the formation of 1:1 covalent adducts have been considered. Various attempts to isolate such adducts via the reaction of an authentic sample of bis(N-triflyl)imidazolium trifate with aldoxime were unsuccessful. Remarkably, whereas isolated benzaldoxime adducts undergo deprotonation/methylation with NaH/MeI, an authentic sample of bis(N-triflyl)imidazolium triflate did not undergo H/Me exchange under these conditions. These transformations are discussed.

Method for producing aromatic nitriles

PCT No. PCT/EP98/00696 Sec. 371 Date Aug. 17, 1999 Sec. 102(e) Date Aug. 17, 1999 PCT Filed Feb. 9, 1998 PCT Pub. No. WO98/37058 PCT Pub. Date Aug. 27, 1998A process for preparing aromatic nitriles from corresponding chloroaromatics by reaction with cyanides.