Methyl 4-bromobenzoate

Esters of 2-acetonylbenzoic acid are formed when methyl 2-bromobenzoates are treated with 7r-(2-methoxyallyl)nickel bromide (77JOC1329). Cyclization to the isocoumarin occurs on treatment with sodium hydride in benzene with a trace of t-butanol (Scheme 183). A... 

If 2-bromo-benzaldehyde or methyl-2-bromobenzoic acid is used as the aryl component, P-quinoline and 3-quinolin-l-one are obtained in moderate yields... 

The synthesis of saprisartan, reported by Judd and co-workers, used a Suzuki reaction as a key step to couple a benzofuran-based boronic acid with methyl 2-bromobenzoate in 30% yield. The resulting compound was then brominated and the methyl ester was hydrolyzed to produce the corresponding acid in 92% yield. Conversion of the acid to the Boc protected amine occurred with 18% yield. A second bromination, followed by substitution with a highly functionalized imidazole, gave the desired intermediate in 60% over two steps. Three additional steps were required to generate saprisartan in 1% overall yield. 

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