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On the reaction of methoxide ion with bromoiodothiophenes

1980; Wiley; Volume: 17; Issue: 1 Linguagem: Inglês

10.1002/jhet.5570170133

1943-5193

Salo Gronowitz, Anders Hallberg, C. GLENNOW,

Synthesis and Reactions of Organic Compounds

Abstract The reaction of 3‐bromo‐2‐iodothiophene with sodium methoxide in methanol, pyridine or hexamethylphosphoric triamide and the same reaction of 4‐bromo‐2‐iodo‐ and 4‐bromo‐3‐iodo‐thiophene in pyridine led to a halogen‐dance, giving the same mixture of 3‐bromothiophene, bromo‐iodothiophenes, diiodo‐bromothiophenes and triiodo‐bromothiophenes. The reaction of all three isomeric bromo‐iodothiophenes with sodium methoxide in methanol in the presence of cupric oxide gave 4‐bromo‐2‐methoxythiophene.