Methyl 2,5-dichloro­benzoate

Tariq Mahmood Babar; Ghulam Qadeer; Nasim Hasan Rama; Ales Ruzicka; Zdenka Padelkova

doi:10.1107/S1600536808029541

. 2008 Sep 20;64(Pt 10):o1970. doi: 10.1107/S1600536808029541

Methyl 2,5-dichlorobenzoate

Tariq Mahmood Babar ^a, Ghulam Qadeer ^a, Nasim Hasan Rama ^a,^*, Ales Ruzicka ^b, Zdenka Padelkova ^b

PMCID: PMC2959309 PMID: 21201170

Abstract

In the molecule of the title compound, C₈H₆Cl₂O₂, the benzene ring is oriented with respect to the planar ester group at a dihedral angle of 39.22 (3)°.

Related literature

For general background, see: Zheng et al. (2003 ▶); Al-Talib et al. (1990 ▶); Yousif et al. (1986 ▶); Ahmad et al. (2001 ▶); Al-Soud et al. (2004 ▶); El-Emam et al. (2004 ▶); Weinstock et al. (1991 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶); and of MOGUL, see: Bruno et al. (2004 ▶). graphic file with name e-64-o1970-scheme1.jpg

Experimental

Crystal data

C₈H₆Cl₂O₂
M _r = 205.03
Triclinic,
a = 3.8452 (3) Å
b = 7.0158 (4) Å
c = 15.8510 (10) Å
α = 77.189 (6)°
β = 89.130 (7)°
γ = 83.741 (5)°
V = 414.46 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 150 (1) K
0.68 × 0.11 × 0.06 mm

Data collection

Bruker–Nonius Kappa CCD area-detector diffractometer
Absorption correction: Gaussian (Coppens, 1970 ▶) T _min = 0.864, T _max = 0.971
5966 measured reflections
1840 independent reflections
1455 reflections with I > 2σ(I)
R _int = 0.110

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.146
S = 1.09
1840 reflections
109 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶)and DENZO (Otwinowski & Minor, 1997 ▶); cell refinement: DIRAX/LSQ (Duisenberg, 1992) ▶); data reduction: EvalCCD (Duisenberg, 1992) ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808029541/hk2533sup1.cif

e-64-o1970-sup1.cif^{(13.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029541/hk2533Isup2.hkl

e-64-o1970-Isup2.hkl^{(90.6KB, hkl)}

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

Acknowledgments

The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan, and also thank the Ministry of Education of the Czech Republic for financial support (project No. VZ0021627501).

supplementary crystallographic information

Comment

The title compound is a lachrymator and a drug intermediate. Methyl 2,5-di- chlorobenzoate is widely employed in synthetic organic chemistry for example, 2,5-dichlorobenzohydrazide, 2,5-disubstituted-1,3,4-oxadiazoles (Zheng et al., 2003; Al-Talib et al., 1990) and 5-substituted-2-mercapto-1,3,4-oxadiazoles (Yousif et al., 1986; Ahmad et al., 2001; Al-Soud et al., 2004; El-Emam et al., 2004). In addition, methyl 4-(bromomethyl)benzoate has been used in the synthesis of 1-(carboxybenzyl)imidazole-5-acrylic acids, which are potent and selective angiotensin II receptor antagonists (Weinstock et al., 1991).In view of the versatility of these compounds, we have synthesized the title compound, and report herein its crystal structure.

In the molecule of the title compound, (Fig. 1), the bond lengths and angles are generally within normal ranges (Cambridge Structural Database, Version 5.28, November 2006; Mogul Version 1.1; Allen, 2002, Bruno et al., 2004). The benzene ring (C1-C6) is oriented with respect to the planar ester group (O1/O2/C1/C7/C8) at a dihedral angle of 39.22 (3)°.

Experimental

For the preparation of the title compound, the mixture of 2,5-dichlorobenzoic acid (2.05 g, 10 mmol) and absolute methanol (50 ml) in the presence of a few drops of suphuric acid was refluxed for 5 h. The excess of solvent was removed by distillation. The solid residue for filltered off, washed with water and recystallized from ethanol (30%) to give the title compound (yied; 88%, m.p. 319-321 K). Suitable single crystals of the title compound were obtained by slow evaporation of an ethanol solution at room temperature.