O-Chlorobenzonitrile

Lithiomethyl-3-phenylquinoxaline (114) and o-chlorobenzonitrile gave 2-(f>-amino-o-chlorostyryl)-3-phenylquinoxaline (115) (no details 28%).973... 

Cations, cyclopropenyl, 54, 97 o-Chlorobenzaldehyde, by reduction of o-chlorobenzonitrile with Raney nickel alloy in formic acid, 51, 23 p-Chlorobenzaldehyde, by redaction of p-chlorobenzonitflle with Raney nickel alloy,1 51, 22... 

Photolytic. When dichlobenil was irradiated in methanol with a 450-W mercury lamp and a Corex filter for 8 h, o-chlorobenzonitrile and benzonitrile formed as the major and minor products, respectively (Plimmer, 1970). 

Condensed 4-halo-1,2,3-triazines are a virtually unknown class of compounds and are apparently very unstable. Reaction of 1,2,3-benzo-triazin-4-one (10, R = H) with a mixture of phosphorus oxychloride and phosphorus pentachloride, for example, results in formation of o-chlorobenzonitrile, presumably via formation and then decomposition of the 4-chlorotriazine (137) to give the diazonium salt (138), subsequent... 

Among the ortho substituted aryl halides, o-dichlorobenzene and o-chlorobenzonitrile did not react while o-fluorochlorobenzene and bro-momesitylene gave the nitrile in poor yield. The highest catalytic efficiency obtained in the case of bromobenzene was about 110 moles of... 

Vierfond et al. used thermal cyclization (79JHC753). The anion obtained by the reaction of quinaldine with phenyllithium was reacted with o-chlorobenzonitrile to afford imine 138, which cyclized at 235°C to give amino derivative 139 (32%). Another method is shown by the reaction of 140-142. The reaction of 140 with excess sodium diethyl malonate in hexamethylphosphoramide (HMPA) at 190°C gave cyclization product 141 (38%), which was converted to fully aromatic 142 by reaction with acetic anhydride (92%) (82JHC127). 

Cyanation of aryl halides to form nitriles is generally robust unless catalyzed by Co, Ni or Pd complexes [167 —171], A useful catalytic mixture comprises NiBr2/Zn/ phosphine/KCN. The use of PPh3 is sufficient to achieve good conversion of chlorobenzene to benzonitrile. But for the more resistant o-dichlorobenzene and o-chlorobenzonitrile, dppf is reported to show better conversion and selectivity [172], The choice of phosphine is obviously crucial as P(o-Tol)3 and dppe are distinctly ineffective. The superiority of dppf over many other phosphines is remarkably evident in the cyanation of aryl triflates and halides when catalyzed by phosphine-doped Pd2(dba)3 [173]. 

The previously described synthesis1 from o-chlorobenzylidene chlorides has been extended to the use of o-chlorobenzonitriles,15 o-chlorobenzalde-hydes,16 and o-chlorophenacyl compounds.17 An example is the preparation... 

It is prepared first by the interaction of o-chlorobenzonitrile and bromo-cyclopentane in the presence of strong alkali to yield an epoxy compound. 

Chlorobenzonitrile CAS 873-32-5 EINECS/ELINCS 212-836-5 Synonyms o-Chlorobenzonitrile OCBN Orthochlorobenzonitrile Empihcai C7H4CIN... 

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