5-Fluoro-2-methylbenzonitrile synthesis
- Product Name:5-Fluoro-2-methylbenzonitrile
- CAS Number:77532-79-7
- Molecular formula:C8H6FN
- Molecular Weight:135.14
953422-44-1
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Yield: 82%
Reaction Conditions:
with trifluoromethylsulfonic anhydride in dichloromethane at 20; for 6 h;Inert atmosphere;
Steps:
General procedure for synthesis of nitriles from oximes (1-16):
General procedure: A mixture of aldoximes (1 mmol) and imidazole (3 mmol) in anhydrous DCM (10-15 mL) was charged into an oven-dried round-bottom flask under nitrogen and the reaction mixture was stirred at r.t. for 20 min, after which triflic anhydride (0.4-1.0 mmol) was added dropwise via syringe under nitrogen, and the reaction mixture was allowed to stir at r.t. for a specific time (Table 1). Progress of the reaction was monitored by TLC and/or by GC-MS. Upon completion, the reaction mixture was quenched with dilute NaHCO3 solution and the product mass was extracted in DCM. The solvent was removed under reduced pressure to yield the crude product which was purified by prep TLC (ethyl acetate-hexane mixture) (80:20), to give the corresponding nitrile (61-88% yield). The structure of the products was confirmed by comparison of their mp or bp, TLC, IR, GC-MS, 1H NMR and 13C NMR data with authentic samples obtained commercially or prepared by literature methods.
References:
Kalkhambkar, Rajesh G.;Bunge, Scott D.;Laali, Kenneth K. [Tetrahedron Letters,2011,vol. 52,# 40,p. 5184 - 5187] Location in patent:supporting information; experimental part
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77532-79-7
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77532-79-7
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