Bromobenzoic methyl ester

The natural occurrence of cycloartane triterpenoids has been reviewed.25 Acid hydrolysis of lyofolic acid, a glucoside from the leaves of Lyonia ovalifolia, afforded lyofoligenic acid (19) whose structure was established by X-ray analysis of the 3a-O-p-bromobenzoate methyl ester.26 The constitution of the genuine aglycone, protolyofoligenic acid (20), was confirmed by interrelation with cycloartenol.27... 

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. 

Bromohenzoic acid ( bromobenzoic acid) [586-76-5] M 201.0, m 251-252 , 254-256 , 257-258 , plC 3.96. Crystallise the aeid from MeOH, or MeOH/water mixture, 90% EtOH and Et20. The methyl ester has m 81° from Et20 or dilute MeOH. The anilide has m 197° (from EtOH). [Male Thorp J Am Chem Soc 35 269 1913, Larrmeek JAm Chem Soc 76 406 1954, Vandenbelt et al. Anal Chem 26 926 1954, Beilstein 9 IV 1017.]... 

C Fusidic acid methyl ester p - bromobenzoate (absolute configuration)... 

C39Hs3Br07, Fusidic acid methyl ester 0-p-bromobenzoate, 33B, 204... 

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... 

When 2-bromobenzoic esters are treated with ir-(2-methoxyallyl)nickel bromide, the acetonyl group is introduced. Reductive cyclization of the methyl 2-acetonylbenzoates yielded isochroman-l-ones (77JOC1329). 

Methyl o-bromobenzoate [610-94-6] M 215.1, b 131.4-132°/16mm, 234-244°/760mm. A solution of the ester in ether is washed with 10% aqueous Na2C03, water, then dried and distilled. [Beilstein 9 H 348, 9 III 1385, 9 IV 1012.]... 

The ready availability of arylboronates by an aromatic C-H borylation provides a synthetic link to the well-established palladium-catalyzed cross-coupling reactions, rhodium-catalyzed 1,4-addition to a,p-unsaturated carbonyl compounds, and other bond forming reactions using arylboronic esters (Scheme 2.12). Borylation of 1,3-dichlorobenzene with pinacolborane is followed directly by a cross-coupling reaction with methyl p-bromobenzoate for the synthesis of a biaryl product in 91% yield [60]. Pinacol esters of arylboronic acids react much slower than the free acids [62], but both derivatives achieve high isolated yields and comparable enantioselectivities (91% ee) in asymmetric 1,4-addition to N-benzyl crotonamides [63]. Borylation of arenes followed by oxidation of the C-B bond is synthetically equivalent to an aromatic C-H oxidation to phenols [64]. Oxidation of the resulting arylboronates with Oxone in a 1 1 acetone-water solution is completed within 10 min at room temperature. 

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