Chemical Properties
slight yellow to white powder
Uses
2-Amino-4-bromobenzoic acid, , is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.
reaction suitability
reaction type: solution phase peptide synthesis
Synthesis
2) Under stirring conditions, 4-bromo-2-nitrobenzoic acid (1.80 g, 7.83 mmol) was dissolved in 0.88 N aqueous sodium hydroxide (10 mL), followed by the sequential addition of ferric (III) chloride (133 mg) and isopropanol (0.7 mL). Hydrazine hydrate (1.1 mL) was slowly added dropwise to the above mixture and the reaction system was warmed up to 75 °C with continuous stirring for 2 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated to give the crude product. The crude product was washed with water to afford 4-bromo-2-aminobenzoic acid (1.73 g, 96% yield). The structure of the product was confirmed by 1H NMR (DMSO-d6): δ 6.62 (dd, J = 1.5, 8.5 Hz, 1H), 6.95 (d, J = 1.5 Hz, 1H), 7.56 (d, J = 8.5 Hz, 1H).
References
[1] Patent: US2004/116422, 2004, A1. Location in patent: Page/Page column 31
[2] Organic Letters, 2011, vol. 13, # 19, p. 5220 - 5223
[3] Journal of Organic Chemistry, 1997, vol. 62, # 5, p. 1240 - 1256
[4] Patent: WO2006/51290, 2006, A2. Location in patent: Page/Page column 111; 144
[5] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443
