Synthesis and Crystal Structure of (2-Hydroxy-5-methylphenyl)-(2-bromophenyl)methanone

Abstract

The efficiency of benzophenone analogues as chemotherapeutic agents, especially as inhibitors of HIV-1 reverse transcriptase RT, cancer 1 and inflammatory, is well established and their chemistry has been extensively studied. Benzophenones are usually obtained from natural products 2 or by synthetic methods. 3 The importance of these substances is basically due to the diverse biological and chemical properties that they possess. Subsequently, benzophenones are frequently used in medicine and industry. In a typical procedure, 1 (10 g, 0.034 mol) was thoroughly mixed with montmorillonite K 10 clay (1:3 w/w) in the solid state using a vortex mixer and subjected to microwave irradiation at 40% power for 5 min. The completion of the reaction was monitored on TLC and the product was extracted into ether. Finally, it was isolated and recrystallized and the yield of 2 was 89%. A schematic diagram of the molecule is shown in Fig. 1. A single crystal of the title compound with dimensions of 0.3 × 0.3 × 0.3 mm was chosen for X-ray diffraction studies. The crystal and experimental details are given in Table 1. The data were collected on the DIPLabo Image Plate system with graphite-monochromated Mo Kα radiation. Thirty six frames of data were collected in oscillation mode with an oscillation range of 5˚ and processed using Denzo. 4 The reflections were merged with Scalepack. All of the frames could be indexed using primitive monoclinic lattice. The structure was solved by direct methods using SHELXS-97.5 The structure was refined by full-matrix least squares method with anisotropic temperature factors for non-hydrogen atoms using SHELXL-97.5 The hydrogen atoms were fixed at chemically acceptable positions, and were refined with isotropic temperature factors. An ORTEP drawing of the molecule with thermal ellipsoids at 40% probability is shown in Fig. 2. The substitution at the 2-position can promote a steric hindrance that results in the large asymmetry of the molecule (viewed along the C=O bond). The title molecule is indeed asymmetric. The bond length C8‐C10 is 1.454(6)A and C5‐C8 x43