ChemicalBook CAS DataBase List 2-Bromo-6-nitrobenzaldehyde

2-Bromo-6-nitrobenzaldehyde synthesis

12synthesis methods

Product Name:2-Bromo-6-nitrobenzaldehyde
CAS Number:20357-21-5
Molecular formula:C7H4BrNO3
Molecular Weight:230.02

N-Bromosuccinimide (NBS) (1.48 g, 8.32 mmol) was added to a solution of 2-Nitrobenzaldehyde (1.01 g, 6.71 mmol) in H2SO4 (concentrated 5.0 mL). The resulting mixture was stirred at ambient temperature (3 h). The reaction was quenched with ice and extracted with ethyl acetate (320mL). The combined organic phases were washed with saturated NaCl (aqueous, 30 mL), dried (MgSO4), and filtered through a silica gel plug, and the solvents were evaporated under reduced pressure. The resulting brown oil was purified by column chromatography (hexanes=EtOAc, 8:2) to afford 2-Bromo-6-nitrobenzaldehyde.

552-89-6
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20357-21-5
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$31.00/100mg

Yield:20357-21-5 92%

Reaction Conditions:

Stage #1: 2-nitro-benzaldehydewith sulfuric acid for 0.166667 h;Cooling;Green chemistry;
Stage #2: with N-Bromosuccinimide at 45; for 0.833333 h;Irradiation;Green chemistry;

Steps:

1 Example 1: Synthesis of Compound (III)

The compound (II) o-nitrobenzaldehyde (0.80 g, 5.30 mmol) and concentrated sulfuric acid (98 wt%, 6.4 ml) were placed in a reaction flask and stirred under a cold well for 10 minutes.Then, NBS (1.13 g, 6.36 mmol) was slowly added and stirred for 5 minutes, and finally transferred to an oil bath at 45 ° C and allowed to react under light for 45 minutes.After the reaction was completed, it was cooled to room temperature, and the reaction mixture was poured into crushed ice and quenched, and then extracted with ethyl acetate (50 ml).Wash with saturated aqueous sodium hydrogencarbonate (50 ml), dry over anhydrous sodiumdry,Obtained 281 mg of bromo o-nitrobenzaldehyde (III) as a brownish yellow solid, yield 92.0%, purity ≥98%.

References:

CN108484623,2018,A Location in patent:Paragraph 0047; 0048; 0049

55289-35-5 Synthesis