2-(5-Bromo-2-methyl­phen­yl)propan-2-ol

Hui Zeng; Xin-Lin Liu

doi:10.1107/S1600536810042698

. 2010 Oct 30;66(Pt 11):o2956. doi: 10.1107/S1600536810042698

2-(5-Bromo-2-methylphenyl)propan-2-ol

Hui Zeng ^a, Xin-Lin Liu ^b,^*

PMCID: PMC3009192 PMID: 21589124

Abstract

The title compound, C₁₀H₁₃BrO, crystallizes with four independent molecules of similar geometry in the asymmetric unit. The crystal packing is stabilized by intermolecular O—H⋯O hydrogen bonds, which link the molecules into tetramers.

Related literature

The title compound is an intermediate for the synthesis of SGLT2 inhibitors, which possess potent antihyperglycemic activity, see: Gao et al. (2010 ▶); Meng et al. (2008 ▶); Wang et al. (2010 ▶).

Experimental

Crystal data

C₁₀H₁₃BrO
M _r = 229.11
Triclinic,
a = 12.074 (2) Å
b = 12.115 (2) Å
c = 15.242 (3) Å
α = 109.51 (3)°
β = 103.52 (3)°
γ = 90.70 (3)°
V = 2033.2 (7) Å³
Z = 8
Mo Kα radiation
μ = 4.00 mm⁻¹
T = 113 K
0.26 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T _min = 0.423, T _max = 0.533
20930 measured reflections
7162 independent reflections
5048 reflections with I > 2σ(I)
R _int = 0.077

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.102
S = 0.94
7162 reflections
450 parameters
H-atom parameters constrained
Δρ_max = 1.36 e Å⁻³
Δρ_min = −1.06 e Å⁻³

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042698/rz2503sup1.cif

e-66-o2956-sup1.cif^{(29.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042698/rz2503Isup2.hkl

e-66-o2956-Isup2.hkl^{(350.4KB, 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
O1—H1⋯O2ⁱ	0.84	1.90	2.742 (4)	179
O2—H2⋯O4ⁱⁱ	0.84	1.91	2.739 (4)	170
O3—H3⋯O1ⁱⁱⁱ	0.84	1.90	2.727 (4)	167
O4—H4⋯O3^iv	0.84	1.90	2.740 (4)	179

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

supplementary crystallographic information

Comment

The title compound, whose crystal structure is reported herein, is an important intermediate for the synthesis of SGLT2 inhibitors possessing potent antihyperglycemic activity (Gao et al., 2010; Meng et al., 2008; Wang et al., 2010).

The asymmetric unit of the title compound consists of four independent molecules of similar geometry (Fig. 1). All bond lengths and angles are not unusual. In the crystal packing, the independent molecules are linked by intermolecular O—H···O hydrogen bonds into tetramers (Table 1).

Experimental

A dried 100-ml round-bottomed flask was charged with 2.43 g (10 mmol) of ethyl 5-bromo-2-methylbenzoate, 30 ml of dried THF and a magnetic bar, flushed with nitrogen and sealed with rubber septum. The flask was cooled with an ice-water bath, then stirring was initiated. Into the flask was slowly added 7.0 ml (21 mmol; 3.0 M in THF) of methyl magnesium chloride through syringe. After addition, the reaction mixture was stirred at this temperature for half an hour. The reaction mixture was poured into 200 ml of cooled water followed by addition of 200 ml of dichloromethane, and the reaction mixture was stirred and filtered off through a pad of celite. The filtrate was collected and the organic phase was separated. The aqueous phase was back-extracted with another 100 ml 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 product as a white solid, which was triturated with petroleum ether to furnish the pure product as colourless crystals after drying in vacuo at room temperature. Crystals suitable for diffraction were obtained by slow evaporation of a solution of the title compound in petroleum ether/dichloromethane (1:5 v/v) at room temperature.