(Z)-Methyl 2-bromomethyl-3-(2-chlorophenyl)acrylate

In the title compound, C11H10BrClO2, the dihedral angle between the benzene ring and the plane of the acrylate unit is 62.1 (1)°. The crystal packing is stabilzed by intermolecular C—H⋯O hydrogen bonds and C—Cl⋯π interactions [Cl⋯centroid = 3.829 (1) Å and C—Cl⋯centroid = 165.3 (1)°].


Experimental
To a stirred solution of methyl 2-((2-chlorophenyl)(hydroxy)methyl)acrylate (4.42 mmol, 1g) in dichloro methane (DCM) was added a 48% hydrobromic acid (8.84 mmol, 0.71 g) solution and then a concentrated sulphuric acid solution (catalytic amount) at 273 K. After stirring overnight at room temperature, the mixture was diluted with DCM and water. The aqueous phase was extracted twice with DCM. The combined organic phase was washed twice with water an then dried with sodium sulphate. Removal of the solvent led to the crude product which was purified through a pad of silica gel (100-200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colorless solid (1.14 g, 90%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethylacetate solution at room temperature.

Refinement
All the H atoms were positioned geometrically, with C-H = 0.93 -0.98 Å and constrained to ride on their parent atom, with U iso (H)=1.5U eq for methyl H atoms and 1.2U eq (C) for other H atoms.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq