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The reaction of 3,4-dibromo-2,5-bis (chloromethyl) thiophene (1a), sufficiently derived from 3,4-dibromothiophene, with several kinds of nucleophiles was investigated. Whereas cyanomethylation of la t...o 3,4-dibromo-2,5-bis (cyanomethyl) thiophene (1b) failed, thiocyanomethylation, bromomethylation, acetoxymethylation, and hydrolysis readily proceeded to afford the corresponding 3,4-dibromo-2,5-bis (thiocyanomethyl) - (1c), bis (hydroxymethyl) - (1d), bis (bromomethyl) - (1e), and bis (acetoxymethyl) thiophenes (1f) in good yields (62-88%). The thiophene (1a) was reacted with aliphatic amines, such as dimethylamine, trimethylamine, pyrrolidine, piperidine, and morpholine, to produce 2,5-bis (aminomethyl) thiophenes (1g-k) in yields varying from 40% to 96%. The reaction of la with pyridine furnished the mono - (1l) and bis-pyridinium salts (1m), respectively, dependent upon the amount of pyridine used. The mono-salt (1l) was, on purification, hydrolyzed to the hydroxymethyl mono-salt (1n) in 76% yield from 1a.続きを見る
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