1-(2-CHLORO-4-NITROPHENYL)ETHAN-1-ONE

Step 5: Synthesis of l-(2-chloro-4-nitrophenyl)ethanone (7) [0189] A suspension of anhydrous magnesium chloride (47 g, 0.214 mol, 0.7 equiv.) in toluene (300 mL) was treated with triethylamine (75.04 mL, 0.535 mol, 2.5 equiv.) and diethylmalonate (41.09 g, 0.257 mol, 1.2 equiv.). The reaction mixture was stirred at RT for 1.5 h. To this was added 2-chloro-4-nitrobenzoyl chloride (6) (47 g, 0.214 mol, 1 equiv.) dropwise (an exothermic reaction up to 50 °C was observed during addition). Toluene (50 mL) was used for complete transfer of 2-chloro-4-nitrobenzoyl chloride to the reaction mixture. The reaction mixture was stirred at RT for 18 h. The reaction was monitored by TLC and NMR. After complete consumption of starting material, concentrated hydrochloric acid (35 percent solution) (300 mL) was added and the upper toluene layer was separated. The toluene was evaporated under reduced pressure below 50 °C. To the residue were added DMSO (200 mL) and water (10 mL), and the mixture heated at 160 °C for 12 h. The reaction was monitored by TLC and NMR. The reaction mixture was allowed to come to RT and water (40 mL) was added. The reaction mixture was extracted with EtOAc (3x200 mL). The EtOAc extracts were combined and washed with brine solution (3x300 mL) and dried over anhydrous sodium sulfate. The EtOAc layer was concentrated to get l-(2-chloro-4-nitrophenyl) ethanone (7) (43 g (84 percent yield)) as a yellow liquid which solidified upon refrigeration. 1H NMR (400 MHz, Chloroform-^/): δ (ppm): 8.29 (d, J = 2.2 Hz, 1H), 8.17 (dd, J= 8.5, 2.1 Hz, 1H), 7.65 (d, J=8.4 Hz, 1H), 2.66 (s, 3H).A suspension of anhydrous magnesium chloride (47 g, 0.214 mol, 0.7 equiv.) in toluene (300 mL) was treated with triethylamine (75.04 mL, 0.535 mol, 2.5 equiv.) and diethylmalonate (41.09 g, 0.257 mol, 1.2 equiv.).

Molecular Weight:199.59
XLogP3:2.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:199.0036207
Monoisotopic Mass:199.0036207
Topological Polar Surface Area:62.9
Heavy Atom Count:13
Complexity:226
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes