2-(4-Bromophenyl)-5,7-dimethyl-3-methylsulfanyl-1-benzofuran

The title compound, C17H15BrOS, was prepared by the Lewis acid-catalysed reaction of 2,4-dimethylphenol with 4′-bromo-2-chloro-2-(methylsulfanyl)acetophenone. The 4-bromophenyl ring is rotated slightly out of the benzofuran plane, making a dihedral angle of 8.4 (1)°. The crystal structure is stabilized by a CH2—H⋯π interaction between the 5-methyl group and the benzene ring of the benzofuran system.

The title compound, C 17 H 15 BrOS, was prepared by the Lewis acid-catalysed reaction of 2,4-dimethylphenol with 4 0 -bromo-2-chloro-2-(methylsulfanyl)acetophenone. The 4-bromophenyl ring is rotated slightly out of the benzofuran plane, making a dihedral angle of 8.4 (1) . The crystal structure is stabilized by a CH 2 -HÁ Á Á interaction between the 5-methyl group and the benzene ring of the benzofuran system.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2192).
The benzofuran unit is essentially planar, with a mean deviation of 0.007 Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle in the title compound formed by the plane of the benzofuran unit and the plane of the 4-bromophenyl ring is 8.4 (1)°. The molecular packing ( Fig. 2) is stabilized by a CH 2 -H···π interaction between 5-methyl group and the benzene ring of benzofuran system, with a C15-H15A···Cg i separation of 2.97 Å (Table 1; Cg is a centroid of the C2-C7 benzene ring, symmetry code as in Fig. 2).

Experimental
Zinc chloride (546 mg, 4.0 mmol) was added at room temperature to a stirred solution of 2,4-dimethylphenol (489 mg, 4.0 mmol) and 4'-bromo-2-chloro-2-(methylsulfanyl)acetophenone (1.12 g, 4.0 mmol) in dichloromethane (30 ml) and stirred for 40 min. The mixture was quenched with water and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (CCl 4 ) to afford the title compound as a colorless solid [yield 52%, m.p. 385-386 K; R f = 0.81 (CCl 4 )]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dilute solution of the title compound in chloroform at room temperature.

Refinement
All H atoms were geometrically located in ideal positions and refined using a riding model, with C-H = 0.95 Å for aromatic H atoms and 0.98 Å for methyl H atoms, and with U iso (H) = 1.2U eq (C) for aromatic H atoms, and 1.5U eq (C) for methyl H atoms.   as large as those based on F, and R-factors based on ALL data will be even larger.