2-Bromo-2'-nitroacetophenone

White to pale yellow crystalline powder

To a stirred mixture of 2′-nitroacetophenone 5 (20 g, 121 mmol) and AlCl3 (500 mg, 3.75 mmol) in dry ether (600 mL) at 0 °C and under argon was added dropwise bromine (6.2 mL, 121 mmol) over 1 h. The reaction mixture was allowed towarm to room temperature andstirred for 3 h (reaction progress monitored by TLC). The organic layer was washed with water (3 × 200 mL), dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography on silica gel (CH2Cl2/petroleum ether, 70:30) to afford 31.7 g of 2-bromo-1-(2-nitrophenyl)ethanone as a yellow solid. The product was crystallised from MeOH to give 26.1 g of pure product. Yield: 88percent. Colorless micro-needles; TLC: Rf (CH2Cl2/petroleum ether, 70:30) 0.4; 1H NMR (400 MHz, CDCl3): δ 8.21 (dd, 3J’8.1 Hz, 4J 1.2 Hz, 1 H, Ar-H’), 7.79 (td, 2 × 3J 7.5 Hz, 4J 1.3 Hz, 1 H, Ar-H’), 7.68 (ddd, 3J 8.1 Hz, 3J 7.5 Hz, 4J 1.6 Hz, 1 H, Ar-H’), 7.50 (dd, 3J 7.5 Hz, 4J 1.6 Hz, 1 H, Ar-H), 4.30 (s, 2 H, CH2); 13C NMR (100 MHz, CDCl3): δ 194.3 (C=O), 145.4 (Ar-C’), 134.9 (Ar-C’), 134.8 (Ar-CH’), 131.3 (Ar-CH’), 129.1 (Ar-CH), 124.5 (Ar-CH), 33.9 (CH2).EXAMPLE 26 General procedure: To a solution of the olefin (0.5–1.2mmol) in 10–16mL of acetonitrile-water (1:1) mixture was added NBS (1.05equiv) at rt. The reaction mixture was stirred until all the olefin was consumed, as monitored by TLC analysis. Subsequently, TetMe-IA (10molpercent) and Oxone (1.0equiv) were introduced into the reaction mixture, and the stirring was continued. After completion of the oxidation as judged by TLC analysis, the reaction mixture was washed with saturated NaHCO

Bromo-2’nitroacetophenone is used in the novel synthesis of 5-pyridylindolizine derivatives.

Molecular Weight:244.04
XLogP3:2.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:242.95311
Monoisotopic Mass:242.95311
Topological Polar Surface Area:62.9
Heavy Atom Count:13
Complexity:214
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes