2,5-Dibromothiophene → 4,7-Dibromo-2,1,3-benzothiadiazole

Participants

Reaction Steps

1,4-Dibromonaphthalene (M-16), 2,5-dibromothiophene (M-11), and 9,10-dibromoanthracene (M-18) are available commercially from Acros Organics, a division of Fisher Scientific Co. or Aldrich Chemicals. 5,5′-dibromo-2,2′-bithiophene (M-12) is prepared by bromination of 2,2′-bithiophene, as reported by R. M. Kellogg, A. P. Schaap, and H. Wynberg in Journal of Organic Chemistry, Vol. 34, pp. 343-346 (1969). 4,7-dibromo-2,1,3-benzothiadiazole (M-15) is prepared by bromination of 2,1,3-benzothiadiazole as reported by K. Pilgram, M. Zupan, and R. Skiles in Journal of Heterocyclic Chemistry, Vol. 7, pp. 629-633 (1970). 3,6-Dibromo-1,2-phenylenediamine is synthesized from 4,7-dibromo-2,1,3-benzothiadiazole as reported for the selenium analog reported by C. W. Bird, G. W. H. Cheeseman, and A. A. Sarsfield in Journal of Chemical Society, pp. 4767-4670 (1963) and was converted to 5,8-dibromo-2,3-diphenylquinoxaline (M-17) as reported in the same reference.

Provenance & Evidence