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

Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee

doi:10.1107/S1600536807063052

. 2007 Dec 6;64(Pt 1):o148. doi: 10.1107/S1600536807063052

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

Hong Dae Choi ^a, Pil Ja Seo ^a, Byeng Wha Son ^b, Uk Lee ^b,^*

PMCID: PMC2915216 PMID: 21200712

Abstract

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.

Related literature

For the crystal structures of similar 2-(4-bromophenyl)-1-benzofuran compounds, see: Choi et al. (2007a ▶,b ▶).

Experimental

Crystal data

C₁₇H₁₅BrOS
M _r = 347.26
Monoclinic,
a = 5.2332 (1) Å
b = 10.6602 (2) Å
c = 13.6374 (2) Å
β = 98.092 (1)°
V = 753.21 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.86 mm⁻¹
T = 296 (2) K
0.30 × 0.24 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T _min = 0.481, T _max = 0.804
7779 measured reflections
3448 independent reflections
2957 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.066
S = 0.87
3448 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), 1477 Friedel pairs
Flack parameter: 0.011 (7)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063052/om2192sup1.cif

e-64-0o148-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063052/om2192Isup2.hkl

e-64-0o148-Isup2.hkl^{(169.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯Cgⁱ	0.96	2.97	3.891 (3)	161

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Symmetry code: (i) Inline graphic . Cg is the centroid of the C2–C7 benzene ring.

supplementary crystallographic information

Comment

As part of our continuing studies on the synthesis and structures of 2-(4-bromophenyl)-1-benzofuran derivatives, the crystal structures of 2-(4-bromophenyl)-5-methyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007a) and 2-(4-bromophenyl)-5,7-dimethyl-3-methylsulfinyl-1-benzofuran (Choi et al., 2007b) have been described to the literature. Herein we report the molecular and crystal structure of the title compound, 2-(4-bromophenyl)-5,7-dimethyl-3-methylsulfanyl-1-benzofuran (Fig. 1).

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 CH₂—H···π interaction between 5-methyl group and the benzene ring of benzofuran system, with a C15—H15A···Cgⁱ 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 (CCl₄) to afford the title compound as a colorless solid [yield 52%, m.p. 385–386 K; R_f = 0.81 (CCl₄)]. 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.