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Synthesis 1986; 1986(9): 735-737
DOI: 10.1055/s-1986-31759
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Convenient Synthesis of 6-Methoxyindole and 6-Methoxytryptophyl Bromide

Paul L. Feldman* , Henry Rapoport
  • *Department of Chemistry, University of California, Berkeley, CA 94720, U.S.A.
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Publication Date:
20 August 2002 (online)

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A preparatively convenient synthesis of 6-methoxyindole (7) and 6-methoxytryptophylbromide (11) is presented starting with p-cresol (1). Regioselctive nitration of p-cresol carbonate (2) followed by hydrolysis of the carbonate and methylation gives 4-methoxy-2-nitrotoluene (5) which is converted to 7 by the Batcho-Leimgruber indole synthesis. Subsequent oxalylation of 7 followed by esterification reduction and bromination yields 6-methoxytryptophyl bromide (11). The overall yield of 7 and 11 from p-cresol is 43% and 25%, respectively.