ChemicalBook CAS DataBase List NITROFEN

NITROFEN synthesis

4synthesis methods

Product Name:NITROFEN
CAS Number:1836-75-5
Molecular formula:C12H7Cl2NO3
Molecular Weight:284.09

350-46-9 Synthesis

350-46-9
513 suppliers
$10.60/1gm:

120-83-2 Synthesis

120-83-2
395 suppliers
$12.90/100g

1836-75-5
137 suppliers
$28.00/100mg

Yield:1836-75-5 68%

Reaction Conditions:

Stage #1: 2,4-dichlorophenolwith sodium hydride in N,N-dimethyl-formamide;mineral oil at 20; for 1 h;
Stage #2: 4-Fluoronitrobenzene in N,N-dimethyl-formamide;mineral oil at 20 - 50; for 13 h;

Steps:

Synthesis of compounds (2a-d)

General procedure: 0.69 g (17.3 mmol) of 60% NaH dispersion in mineral oil was washed with hexane and suspended in 20 ml DMF. The solution of corresponding phenol (12.9 mmol) in DMF (20 ml) was then added dropwise. After stirring for 1h at room temperature the solution of 4-nitrobenzene (1.5g, 10.3 mmol) in DMF (4 ml) was added. After further stirring for 1h at room temperature the mixture was heated for 12h at 50 °C. After reaction was complete the reaction mixture was saturated by the solution of NH4Cl. The mixture was extracted with diethyl ether. The organic layer was washed with 0.2 M solution of NaOH until bleaching of the water layer and then washed by 1 M solution of HCl and brine.The organic layer was dried over anhydrous MgSO4. The resulting solution was concentrated in vacuo and purified using column chromatography with hexane-ethyl acetate (5:1) as the eluent to give compounds 2a-d with the following characteristics:

References:

Antipin, Roman L.;Beshnova, Daria A.;Petrov, Rostislav A.;Shiryaeva, Anna S.;Andreeva, Irina P.;Grigorenko, Vitaly G.;Rubtsova, Maya Yu.;Majouga, Alexander G.;Lamzin, Victor S.;Egorov, Alexey M. [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 7,p. 1588 - 1592] Location in patent:supporting information