ChemicalBook CAS DataBase List 2-Bromo-5-chloronitrobenzene

2-Bromo-5-chloronitrobenzene synthesis

7synthesis methods

Product Name:2-Bromo-5-chloronitrobenzene
CAS Number:41513-04-6
Molecular formula:C6H3BrClNO2
Molecular Weight:236.45

6280-88-2

41513-04-6

General procedure for the synthesis of 2-bromo-5-chloronitrobenzene from 4-chloro-2-nitrobenzoic acid: In a 25 mL round-bottomed flask, fitted with a Dimroth condenser (cooled to 10 °C), 4-chloro-2-nitrobenzoic acid (1.8 mmol), chloroisocyanuric acid ester, brominating agent and solvent (8 mL) were added. The reaction mixture was stirred and heated in an oil bath under fluorescent room light (FL) irradiation. Upon completion of the reaction, the cooled mixture was filtered through a short silica gel pad, washed with 1 M aqueous Na2SO3, dried over anhydrous Na2SO4, filtered and concentrated in vacuum to give 2-bromo-5-chloronitrobenzene. The product may contain 1-5% of 2-chloro-5-nitrobenzene as a by-product. The experimental results are detailed in Table 2. Table 2. Results of bromocarboxylation of nitroaromatic carboxylic acids

6280-88-2 Synthesis

6280-88-2
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41513-04-6
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Yield:41513-04-6 96%

Reaction Conditions:

with trichloroisocyanuric acid;bromine in tetrachloromethane at 10 - 100; for 18 h;Photolysis;

Steps:

4 Bromodecarboxylation of nitroarenecarboxylic acids

General procedure: A 25 mL round bottom flask equipped with Dimroth condenser (chilled to 10 °C) was charged with nitroarenecarboxylic acid ArC0₂H (1.8 mmol), chloroisocyanurate, brominating agent and solvent (8 mL). The mixture was stirred and heated in an oil bath under fluorescent room light irradiation (FL). The cooled reaction mixture was filtered through short silica gel pad, washed with 1 M aq Na₂S0₃, dried over Na₂S0₄, filtered and concentrated in vacuo to obtain bromonitroarene ArBr. The obtained product contained between 1-5% of the corresponding chloronitroarene ArCl as a by-product. The results are presented in Table 2. Table 2. Bromodecarboxylation of nitroarenecarboxylic acids ArC0₂H ^a

References:

WO2017/60906,2017,A1 Location in patent:Paragraph 00122

89-63-4 Synthesis