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

HRID 2163839Notes

Reaction equation

HRID 2163839 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Br:13])[CH:9]=2)[CH:4]=1.CCC(C(C(O)=O)(C)C)C1C=CC2C=C(OC)C=CC=2C=1.OC1C=CC2C(=CC=CC=2)C=1C(O)=O.[N+](=C)=[N-].[CH3:52][O:53][C:54](C1C2C(=CC=CC=2)C=CC=1OC)=[O:55].BrBr>C(O)(=O)C>[CH3:52][O:53][C:54]([C:4]1[C:5]2[C:10](=[CH:9][C:8]([Br:13])=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[O:2][CH3:1])=[O:55]

Participants

8

Reactant 6

HCID 9550DiazomethaneHCID 10599MethallenestrilHCID 167902-Hydroxy-1-naphthoic acidHCID 24408BromineHCID 787862-Bromo-6-methoxynaphthalene2×HCID 604022Methyl 2-methoxy-1-naphthoate

Product 1

HCID 541555836-Bromo-2-methoxy-naphthalene-1-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Sources & evidence

ORD record
ord-6cbd519582b44754927c91dbf7cf4ddb
Source dataset
uspto-grants-1979_01
Patent number
US04137272

Reaction notes

Loading…