Methyl 5-(2-bromoacetyl)-2-propoxybenzoate

The title compound, C13H15BrO4, was synthesized from methyl 5-acetyl-2-hydroxybenzoate. With the exception of the ester group and some H atoms, the molecule is planar, the average deviation from planarity being 0.086 (5) Å. The dihedral angle between the phenyl ring and the ester group is 41.6 (3)°. Adjacent molecules are interconnected by C—H⋯O bonds, generating a layered structure.

The title compound, C 13 H 15 BrO 4 , was synthesized from methyl 5-acetyl-2-hydroxybenzoate. With the exception of the ester group and some H atoms, the molecule is planar, the average deviation from planarity being 0.086 (5) Å . The dihedral angle between the phenyl ring and the ester group is 41.6 (3) . Adjacent molecules are interconnected by C-HÁ Á ÁO bonds, generating a layered structure.

Comment
Methyl 5-acetyl-2-hydroxybenzoate is a common chemical intermediate, which can be easily obtained (Gronnow et al., 2005). It is widely used for the design and synthesis of biological compounds. Biological activities, such as antiulcer (Watanabe et al., 1984) and antihypertensive (Grisar et al., 1981) effects of methyl 5-acetyl-2-hydroxybenzoate derivatives have been reported. In our research, the title compound, (I) (Fig. 1) is an important intermediate used to synthesize variety of compounds, which might have an inhibitive effect on PDE5. Considerable attention has been devoted to the biological activities of methyl 5-acetyl-2-hydroxybenzoate derivatives, however, the crystal structure of the title compound has not been reported, yet. In this work, we present the crystal structure of the title compound.
The molecule is planar with the average deviation from the planarity of 0.086 (5) Å. However, the ester group is out of this plane. The dihedral angle between the phenyl and the ester group is 41.65°.
Packing analysis of the crystal structure shows that molecules are intercontacted by weak C-H···O interactions generating a layered structure (Table 1, Fig. 2).

Experimental
Methyl 5-acetyl-2-propoxybenzoate was obtained by the alkylation of methyl 5-acetyl-2-hydroxybenzoate. To a mixture of methyl 5-acetyl-2-propoxybenzoate (1 mmol), aluminium trichloride (0.15 mmol) and dichlormethane (15 mL), bromine (1.1 mmol) was added dropwise during 15 min at 273 K. The mixture was stirred at room temperature for 10 h. The resulting mixture was washed by aqueous solution of sodium thiosulfate, saturated salt solution, dried by anhydrous sodium sulfate, then the solvent was distilled off. Single crystals suitable for X-ray analysis (m.p. 379 K) were obtained by slow evaporation of solvent mixture of dichlormethane and methanol at room temperature.

Refinement
H atoms were positioned geometrically and refined as riding atoms, with C-H = 0.96Å and U iso (H) = 1.5U eq (C) for methyl H atoms, 0.97Å and U iso (H) = 1.2U eq (C) for methylene H atoms, and C-H = 0.93Å and U iso (H) = 1.2U eq (C) for all other H atoms. Fig. 1. The molecular structure of (I), with atom labels and the 30% probability displacement ellipsoids for non-H atoms.