The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Fluorocyano-benzenes and -pyridines》. Authors are Finger, G. C.; Dickerson, D. R.; Adl, Touradj; Hodgins, T..The article about the compound:6-Fluoronicotinonitrilecas:3939-12-6,SMILESS:N#CC1=CC=C(F)N=C1).Safety of 6-Fluoronicotinonitrile. Through the article, more information about this compound (cas:3939-12-6) is conveyed.
Chlorobenzonitriles stirred and heated at 160-200° with anhydrous KF in Me2SO2 (CA 57, 12358i; 59, 1585a) gave 50-80% of the following I (R = mono- or disubstituted) (R and m.p. CN or b.p./mm. given): 2-F, 103°/35; 4-F, 38°; 2,4-F2, 46°; 2,6-F2, 99°/20; 2-F-5-CF3 (II), 99°/27. Similarly, 2-chloro-pyridinecarbonitriles afforded 54-88% of the following III (R = CN) derivatives (R and m.p. given): 3-CN, 30°; 4-CN, 33°; 5-CN, 51°; 6-CN, 34°. 3-Bromo-4-chloro-α,α,α-trifluorotoluene heated at 145° for 42 hrs. with excess CuCN and KF in HCONMe2 produced 57% II and 43% I (R = 4-5-Cl-CF3), m. 39°.
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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem