5-Bromo-2,4,6-trimethyl-3-methylsulfinyl-1-benzofuran

In the title compound, C12H13BrO2S, there are two symmetry-independent molecules, A and B, in the asymmetric unit. The crystal studied was an inversion twin with a 0.70 (2):0.30 (2) domain ratio. The methylsulfinyl group in molecule B is disordered over two positions with site-occupancy factors fixed at 0.6 and 0.4. The crystal structure is stabilized by C—H⋯O hydrogen bonds and intermolecular C—H⋯π interactions. In addition, the crystal structure exhibits C—Br⋯π interactions, with C—Br⋯Cg1 = 3.646 (8) Å where Cg1 is the centroid of the furan ring.

In the title compound, C 12 H 13 BrO 2 S, there are two symmetryindependent molecules, A and B, in the asymmetric unit. The crystal studied was an inversion twin with a 0.70 (2):0.30 (2) domain ratio. The methylsulfinyl group in molecule B is disordered over two positions with site-occupancy factors fixed at 0.6 and 0.4. The crystal structure is stabilized by C-HÁ Á ÁO hydrogen bonds and intermolecular C-HÁ Á Á interactions. In addition, the crystal structure exhibits C-BrÁ Á Á interactions, with C-BrÁ Á ÁCg1 = 3.646 (8) Å where Cg1 is the centroid of the furan ring.
The benzofuran unit is essentially planar, with a mean deviation of 0.012 (6) Å for A and 0.0022 (7) Å for B, respectively, from the least-squares plane defined by the nine constituent atoms. The crystal studied was an inversion twin with a 0.70 (2):0.30 (2) domain ratio. The O4=S2-C24H 3 group in molecule B is disordered over two positions with site-occupancy factors fixed at 0.4 (for atoms labelled A) and 0.6 (for atoms labelled B) in Fig. 1. The crystal structure is stabilized by three intermolecular C-H···O hydrogen bonds ( Fig. 2 and Table 1; symmetry codes as in Fig. 2). The molecular packing ( Fig. 2) is further stabilized by a intermolecular C-H···π interactions, with a C9-H9A···Cg2 iii separation of 3.30 Å ( Fig.   2 and Table 1; Cg2 is the centroid of the C2-C7 benzene ring, symmetry code as in Fig. 2). In addition, the molecular packing exhibits an intermolecular C-Br···π interaction between the Br atom and the furan ring, with a C16-Br2···Cg1 iv separation of 3.646 (8) Å ( Fig. 2; Cg1 is the centroid of C13-C14/C19/O3/C20 furan ring, symmetry code as in Fig. 2).
Experimental 3-Chloroperoxybenzoic acid, 77% (197 mg, 0.88 mmol) was added in small portions to a stirred solution of 3-methylsulfanyl-2-phenyl-1-benzofuran (228 mg, 0.8 mmol) in dichloromethane (30 ml) at 273 K. After stirring for 3 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography (ethyl acetate) to afford the title compound as a colorless solid [yield 79%, m.p. 400-401 K; R f = 0.61 (ethyl acetate)].
Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in acetone at room temperature.

Refinement
All H atoms were geometrically positioned and refined using a riding model, with C-H = 0.93 Å for aromatic H atoms, 0.96 Å for methyl H atoms, respectively, and with U iso (H) = 1.2Ueq(C) for aromatic H atoms and 1.5Ueq(C) for methyl H atoms.
The crystal studied was an inversion twin with a 0.70 (2)