5-chloro-2-methyl-4-nitroBenzonitrile synthesis
- Product Name:5-chloro-2-methyl-4-nitroBenzonitrile
- CAS Number:101495-54-9
- Molecular formula:C8H5ClN2O2
- Molecular Weight:196.59
557-21-1
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Yield:101495-54-9 82%
Reaction Conditions:
with tetrakis-(triphenylphosphine)-palladium;anhydrous sodium carbonate in N,N-dimethyl-formamide at 50; for 24 h;Inert atmosphere;
Steps:
2 Step 2 - 5-Chloro-2-methyl-4-nitrobenzonitrile
To a mixture of 1-chloro-5-iodo-4-methyl-2-nitro-benzene (11.6 g, 39.2 mmol), Pd(PPh3)4 (4.53 g, 3.92 mmol) and Na2CO3 (8.31 g, 78.4 mmol) in DMF (80 mL) was added Zn(CN)2 (2.76 g, 23.5 mmol, 1.49 mL). The reaction mixture was stirred at 50 °C for 24 hrs under N2. On completion, the reaction mixture was diluted with water (500 mL) and extracted with EA (3 x 300 mL). The organic layer was washed with brine (3 x 300 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (PE:EA=1:0 to 80:1) to give the title compound (6.30 g, 82% yield) as yellow solid.1H NMR (400 MHz, CDCl3) d 7.82 - 7.79 (m, 2H), 2.64 (s, 3H).
References:
WO2020/264499,2020,A1 Location in patent:Paragraph 003492; 003495-003496
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