A NON CLASSICAL REACTION OF 2(3)- BROMOMETHYL-3(2)-NITROTHIOPHENES TOWARDS BASES

References

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• Typical procedure: To a well stirred solution of o-bromomethylnitrothiophene 1 or 4 (2.22 g; 10 mmol) in 50 ml of dry THF at room temperature was added in three portions sodium methoxide (0.6 g; 11.1 mmol) or potassium salt of pyrrole (1.17 g; 11.1 mmol) (prepared by reaction of potassium metal and pyrrole in dry THF). After 15 minutes of reaction, the yellow precipitate formed was collected by filtration, washed with diethyl ether and recrystallized from anhydrous methanol to yield compound 3 or 5 in 75 and 67% respectively
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• Selected data for compound 3: mp 226°C (decomp); 1H NMR (DMSO-d6) δ: 4.65 (s, 1H, H3), 7.10 (d, J = 5.3 Hz, 1H, H4), 7.95 (d, J = 5.3 Hz, 1H, H5); 5C NMR (DMSO-d6) δ: 56.7, 126.2, 134.2, 140.4, 148.3; MS (EI) m/z 282 (10), 141 (90), 113 (70), 85 (100), 70 (70), Anal. Calcd. for C10H6N2O4S2: C, 42.55: H, 2.14; N, 9.92. Found: C, 42.18; H, 1.85; N, 9.67
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