Synthesis p. 735 - 737 (1986)
Update date:2022-08-03
Topics:
Feldman, Paul L.
Rapoport, Henry
A preparatively convenient synthesis of 6-methoxyindole (7) and 6-methoxytryptophylbromide (11) is presented starting with p-cresol (1).Regioselective 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 esterification, reduction and bromination yields 6-methoxytryptophyl bromide (11).The overall yield of 7 and 11 from p-cresol is 43percent and 25percent respectively.
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