Bromobenzoic acid

Tlie mixture is hrmiglit into a lliick-wallcd tube, closed at one end, mil sealetl in the usual way. The tube is heated in the 

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It is worth noting that the Ullmann-Goldberg condensation of aryl halides with phenols and anilines worked efficiently in the presence of copper in water.50 For example, the coupling of 2-chlorobenzoic acid with 4-chlorophenol (K2C03/pyridine/copper powder) gave 2-(4-chlorophenoxy)carboxylic acid (Eq. 6.23).51 The Cu(I)-catalyzed transformation of 2-bromobenzoic acid into salicylic acid has also been studied in aqueous media (Eq. 6.24).52... 

CENTRAL RING CONTAINING ONE HETEROATOM Reaction of 2-bromobenzoic acid (1) with chloroSulfonic acid proceeds to afford the sulfonyl chloride 2 treatment with dimethylamine leads to the corresponding sulfonamide (3). Condensation of bromoacid 3 with the anion from thiophenol in the presence of copper powder results in displacement of halogen by sulfur... 

Benzoic acid, see Anthracene, Biphenyl, 2-Bromobenzoic acid, 2-Bromobenzoic acid, 4-Bromobenzoic acid, 2-Chlorobenzoic acid, 3-Chlorobenzoic acid, 3,5-Dichlorobenzoic acid, Di-n-butyl phthalate, Dicamba, Ethylbenzene, Fluoranthene, 3-Iodobenzoic acid. Naphthalene, Styrene, Permethrin, Toluene, 2,3,6-Trichlorobenzoic acid, oXylene, ro-Xylene, p-Xylene... 

Mefenamic acid Mefenamic acid, A -(2,3-xylyl)anthranylic acid (3.2.19), is synthesized in basically the same manner, by the reaction of the potassium salt of 2-bromobenzoic acid with 2,3-dimethylaniline in the presence of copper (11) acetate [80,81]. 

Commercial 2-bromobenzoic acid, purchased from Aldrich Chemical Company, Inc., is a gray powder, m.p. 144-147°, and was purified as follows the crude acid was dissolved in warm 2N sodium hydroxide solution the mixture was heated to reflux, treated with activated carbon, filtered, and cooled, and the filtrate was acidified with concentrated hydrochloric acid. The colorless solid that precipitated was collected by filtration under reduced pressure and recrystallized from aqueous methanol to give pure 2-bromobenzoic acid as colorless needles, m.p. 148-150°. The checkers used 2-bromobenzoic acid of m.p. 151-151.5°, obtained from Wako Pure Chemical Industries, Ltd., Japan, without further purification. Their results were comparable to those of the submitters. 

The present method of preparation is that described by Bruggink and McKillop.4 It has the particular advantages of high yield and manipulative simplicity, and avoids the problem inherent in Hurt-ley s procedure of separation of mixtures of carboxylic acids by fractional crystallization or column chromatography. The method is, moreover, of wide applicability with respect to both the /3-dicarbonyl compound and the 2-bromobenzoic acid. The synthetic scope and limitations of this procedure for the direct arylation of... 

Synthesis By condensation of 2-bromobenzoic acid with 2,6-dichloro-3-methylaniline by means of CuBr2 in diethyleneglycol dimethyl ether containing N-ethylmorpholine, and heating at 145-155 °C (Scherrer and Short (Parke Davis), 1961 1967) Juby et al., 1968 Arrigoni-Martelli, 1978b Kleemann et al., 1999). 

Bromination of l,2-dihydro-l-methylbenzo[d][l,2,3]diazaborine (188 X = Y = H) gave substitution in the 4-position to give (188 X = Br, Y = H). Oxidation of the brominated product with potassium permanganate led to the isolation of 2-bromobenzoic acid, which was erroneously taken as evidence for bromination in the 5-position. However, a more careful oxidation gave benzoic acid, suggesting that the original procedure oxidized the bromine atom to elemental bromine, which then carried out a deboronating bromination. 

A systematic investigation of the copper-catalyzed reaction between 2-bromobenzoic acid and the anions of 1,3-dicarbonyl compounds has established the optimum conditions for the direct arylation of the /3-dicarbonyl moiety (75T2607). The use of sodium hydride as the base and copper(I) bromide as catalyst is recommended. The absence of a protic solvent ensures that competitive attack on the bromobenzoic acid by a solvent-derived base leading to a salicylic acid is eliminated. For larger scale reactions the addition of toluene offers some practical advantages. 

A greater variety of substituted isocoumarins is available from the reaction of 7r-allylnickel halides with the sodium salts of 2-bromobenzoic acids. Use of the sodium salt is necessary to prevent debromination through an intramolecular proton transfer from the carboxyl group. The initial products, 2-allylbenzoic acids, undergo a palladium-assisted ring closure to isocoumarins. 

Bromo-3-nitrobenzoic acid has been prepared by the nitration of 2-bromobenzoic acid, the 2,3 acid being separated from the 2,5 acid, which is the principal product of the nitration, by fractional crystallization of the potassium salts from water.1... 

V-Methylbenzamide and 2-bromobenzoic acid were similarly converted to the 2-alkyltelluro-substituted compounds1. 

Bromine adds to the alkene but substitutes on the aryl ether, evolving gaseous HBr. 17.10. Strong acid is used for nitration, and the amino group of aniline is protonated to a deactivating — NH3+ group. 17.12. (a) 2,4- and 2,6-dinitrotoluene (b) 3-chloro-4-nitrotoluene and 5-chloro-2-nitrotoluene (c) 3- and 5-nitro-2-bromobenzoic acid ... 

Carboxydiphenylamine-6 -arsinic acid is obtained when 2)-bromobenzoic acid is used in the foregoing. It crystallises from dilute acetic acid in needles, decomposing at 210° C., and is less soluble in cold alcohol or acetic acid than the preceding acids. 

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