(5-Bromo-2-methylphenyl)(4-ethoxyphenyl)methanone

In the title compound, C16H15BrO2, the dihedral angle between the benzene rings is 68.5 (2)°. In the crystal structure, molecules are linked by weak C—H⋯O hydrogen bonds into chains parallel to the b axis.

In the title compound, C 16 H 15 BrO 2 , the dihedral angle between the benzene rings is 68.5 (2) . In the crystal structure, molecules are linked by weak C-HÁ Á ÁO hydrogen bonds into chains parallel to the b axis.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2475).

Comment
Dapagliflozin is an anti-diabetic agent through the inhibition of renal SGLT2, which was developed by Bristol-Myers Squibb Company and is now in the phase III clinical trial (Meng et al., 2008). During the discovery of our own SGLT2 inhibitors as anti-diabetic agents, we prepared the derivatives of dapagliflozin (Meng et al., 2008) for biological evaluation, and the title compound, (5-bromo-2-methylphenyl)(4-ethoxyphenyl)methanone, was prepared as an important intermediate.
In title compound, C 16 H 15 BrO 2 , bond lengths are normal (Allen et al., 1987)). The dihedral angle between the benzene rings (C2-C7 and C9-C14) is 68.5 (2)°. In the crystal structure, molecules interact through weak C-H···O hydrogen bonds to form chains parallel to the b axis.

Experimental
A round-bottomed flask was charged with 2.15 g (10 mmol) of 5-bromo-2-methylbenoic acid, 1 drop of DMF, 1.27 g (10 mmol) of oxalyl chloride and 3 ml of dried dichloromethane, and the mixture was stirred at room temperature over night until a clear solution formed. The reaction mixture was evaporated on a rotary evaporator to give crude 5-bromo-2-chlorobenzoyl chloride, which was dissolved in 15 ml of dried dichloromethane. The solution thus obtained was stirred while being cooled with an ice-salt bath, and 1.22 g (10 mmol) of phenetole was added followed by the addition of 1.60 g (12 mmol) of anhydrous aluminium chloride in a portionwise manner. The resulting mixture was stirred at this temperature for 1 h and poured into 150 ml of ice-water. The mixture formed was extracted with three 50 ml portions of dichloromethane, and the combined extracts were washed with saturated brine, dried over sodium sulfate and evaporated on a rotary evaporator to afford the crude title compound. Pure title compound was obtained by column chromatography. Crystals suitable for X-ray diffraction were obtained through slow evaporation of a solution of the pure title compound in ethyl acetate/petroleum ether (1/5 v/v).

Refinement
All H atoms were found on difference Fourier maps, and included in the final cycles of refinement using a riding model, with C-H = 0.95-0.99 Å and with U iso (H) = 1.2U eq (C) for aryl and methylene H atoms and 1.5U eq (C) for the methyl H atoms. Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 40% probability level.