All articles of this category 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.
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Feldman et al. (1986) studied this question.