Halogeno‐substituted 2‐ and 3‐methylbenzo[b]thiophenes: Use of 1H NMR spectral analysis and 1H{1H} nuclear Overhauser effect for locating the halogen substituent

Ma Rosa Cuberes, Marcial Moreno‐Mañas, Francisco Sánchez‐Ferrandom

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Abstract

Thirty‐seven halogeno‐substituted 2‐ and 3‐methyl‐(or halogenomethyl)‐benzo [b]thiophenes, including 17 new compounds, were prepared. The constitution of 14 of these was confirmed by full analysis (LAOCOON) of their 80 MHz1HNMR spectra and by 1H{1H} NOE measurements. In this way a by‐product from the preparation of 4‐ and 6‐bromo‐3‐bromomethylbenzo[b]thiophenes was shown conclusively to be 5‐bromo‐3‐bromomethylbenzo[b]thiophene. The 3‐substituted benzo[b]thiophenes showed greater NOE enhancement factors at H‐4 than at H‐2 when the 3‐methyl or halogenomethyl substituent was irradiated. Copyright © 1985 Wiley Heyden Ltd
Original languageEnglish
Pages (from-to)814-821
JournalMagnetic Resonance in Chemistry
Volume23
Issue number10
DOIs
Publication statusPublished - 1 Jan 1985

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