2-Bromo-4-chlorobenzoic acid

Synthesis

The crude acid (11a or 12a; 1.0 g) was dissolved in concentrated H2SO4 (10 cm3) and stirred for 5 h, then poured into 50 cm3 of ice water. The product was separated and washed with 5% Na2CO3 solution. The crude anthrone was dissolved in 30 cm3 of acetic acid. 2.00 g of saturated aqueous K2Cr2O7 solution was added, and the mixture was heated to 90°C for 1 hour. After cooling, the mixture was poured into 200 cm3 of water. The separated solid was filtered, chromatographically analyzed on a silica gel column (benzene, then chloroform), and purified by crystallization to give 2-bromo-4-chlorobenzoic acid. 13, yield (85.2%). M, p. 156-158°C, formula: (C7H4BrClO2), analytical results (%): C 35.51, H 1.80, NMR data: C (35.71), H (1.71). Infrared data: IR (cm⁻¹): 3100 (OH) 1705 (C=0); ¹H NMR δH (200 MHz, dimethyl sulfoxide-d⁶) = 13.5 (br s, ¹H, COOH), 7.88 (d, ¹H, J = 2.1 Hz, 3-Ar-H), 7.78 (d, ¹H, J = 8.4 Hz, 5-Ar-H), 7.57 (dd, ¹H, J1 = 2.1 Hz, J2 = 8.3 Hz, 6-Ar-H) ppm. alt="Synthetic route of 2-bromo-4-chlorobenzoic acid">

Figure 2-bromo-4-chlorobenzoic acid synthetic route

Uses

2-Bromo-4-chlorobenzoic acid is used in the production of pharmaceuticals, dye carriers, plasticizers, fragrances, and food preservatives. It is also used to improve the performance of alkyd resin coatings. Furthermore, it is used as an antifungal and disinfectant, serving as a chemical reagent and preservative. 2-Bromo-4-chlorobenzoic acid is commonly used as a fixative or preservative. It is also used as a flavoring agent in fruit juice beverages. Additionally, it can be used in flavorings for chocolate, lemon, orange, berry, nut, and candied fruit.

Chemical Properties

off-white powder