Diazomethane → 6-Bromo-2-methoxy-naphthalene-1-carboxylic acid methyl ester

Participants

Reaction Steps

2-Alkoxy-6-bromo-naphthalenes, especially 2-methoxy-6-bromo-naphthalene, are important starting compounds for the production of pharmaceutical products, especially synthetic estrogens, such as methallenestril (see The Merck Index, 8th Edition, (1968), page 669). For the production of 2-methoxy-6-bromo-naphthalene, 2-hydroxy-naphthalene-1-carboxylic acid was converted with diazomethane into 2-methoxy-naphthalene-1-carboxylic acid methyl ester, the latter was brominated with bromine in acetic acid to form 6-bromo-2-methoxy-naphthalene-1-carboxylic acid methyl ester, then the carboxylic acid methyl ester group was hydrolyzed, and the resulting 6-bromo-2-methoxy-naphthalene-1-carboxylic acid was decarboxylated to form 2-methoxy-6-bromo-naphthalene (see J. Chem. Soc. 1941, 687 + 688).

Provenance & Evidence