5-Bromo-2-hydroxybenzoic acid

Bromo-4,6-Dinitro-Hydroxybenzoic Acid, Calcium Salt. Ca [OOCC6 H(OHXBr)(N02 )2 ] 2... 

Nitration of ///-hydroxybenzoic acid with filming nitric acid in the presence of sulfuric acid and acetic anhydride gives a mixture of the 2-nitro [602-00-6] and 4-nitro [619-14-7] substitution products. Bromination and iodination yield the 4-halogenated derivatives (4-bromo [14348-38-0] and 4-iodo [58123-77-6]). When ///-hydroxybenzoic acid is treated with formalin in the presence of hydrochloric acid, 4-hydroxyphthalide [13161 -32-5] is obtained as shown in equation (10). 

C7H4BrNOS 6-bromo-2-benzothiazolinone 62266-82-4 25.00 1 7496 2 9753 C7H4CI203 3,5-dichloro-4-hydroxybenzoic acid 3336-41-2 25.00 1.5059 2... 

Juch, ibid. 26, 839 (1905) Brunner, Ann. 351, 321 (1907) Zeltner, Landau, Ger. pat. 258,887 Frdl. 11, 210 Dyson, Man mo/ of Organic Chemistry vol. 1 (London, 1950) p 614 by oxidstion of salicylic acid with potassium persulfate Ger, pat. 81,297 (to Schering AG) Frdl 4, 127 from p-hydroxyphenol Meyer, U.S. pat. 2,580,336 (1952 to Monsanto) from 5 -bromo -2 -hydroxybenzoic acid Lowen -thal. Pepper, J. Am. Chem. See. 72, 3292 (1950) by Kolbe synthesis Clemens, U.S. pet. 2,816,137 (1957 to Eastman Kodak). Metabolic product of Pertici/fium patulum Tanen -baum, Bassett, Biochim. Biophys. Acta 28, 21 (1958) of Poty-porus tumulosus Cooke Crowden, Ralph, Amt, J. Chem. 14, 475 (1961). Biosynthesis Oaten back, Linnroth, Acta Chem. Scand. 16, 2298 (1962). 

Hydroxybenzo[6]thiophene-2-carboxylic acid is nitrated152 and nitrosated497 in the 4-position. Dibromination in the presence of acetate ion affords the 4,6-dibromo derivative.421 Likewise, 3-bromo-... 

Further bromination of 3,4,6-tribromo-5-hydroxybenzo[6]thio-phene affords the 2,3,4,6-tetrabromo derivative in the absence of acetate ion, and 3,4,4,6-tetrabromo-4,5-dihydrobenzo[6]thiophen-5-one in the presence of acetate ion. 421 On treatment of 3,4-dibromo-, 4,6-dibromo-, 3,4,6-tribromo-, or 2,3,4,6-tetrabromo-5-hydroxybenzo-[6]thiophene with nitric acid in acetic acid, the corresponding unstable orange crystalline 4-bromo-4-nitro-4,5-dihydrobenzo[6]thio-phen-5-one is obtained.152,421 Hence, once both positions ortho to the hydroxyl group in 5-hydroxybenzo[6]thiophene are occupied by bromine, the properties of these compounds are analogous to the properties of l-bromo-2-naphthol which, on bromination in acetic acid in the presence of acetate ion, affords l,l-dibromo-l,2-dihydro-naphthalen-2-one whereas, in its absence, it affords l,6-dibromo-2-naphthol.616 The behavior of l-bromo-2-naphthol and its derivatives on nitration is similar to that of 4,0-dibromo-5-hydroxybenzo[6]thio-phene and its derivatives.162,616... 

How would you prepare the following compounds from the named starting material (a) 1-methoxy-3-nitrobenzene from ben-zenesulfonic acid (b) methyl 2-hydroxybenzoate from phenol (c) 2-bromo-4-methylphenol from toluene. 

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