ChemicalBook CAS DataBase List 1-CHLORO-2,4-DIMETHYL-5-NITRO-BENZENE

1-CHLORO-2,4-DIMETHYL-5-NITRO-BENZENE synthesis

5synthesis methods

Product Name:1-CHLORO-2,4-DIMETHYL-5-NITRO-BENZENE
CAS Number:69383-68-2
Molecular formula:C8H8ClNO2
Molecular Weight:185.61

2124-47-2 Synthesis

2124-47-2
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69383-68-2
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Yield:69383-68-2 72%

Reaction Conditions:

Stage #1: 5-nitro-2,4-dimethylanilinewith hydrogenchloride;sodium nitrite in water at 0; for 1 h;
Stage #2: with copper(l) chloride in water at 0 - 20; for 11 h;

Steps:

1 Step 1

To a solution of 2,4-dimethyl-5-nitroaniline (500 mg, 3.01 mmol, 1 .00 eq) in concentrated hydrochloric acid (9.00 mL) was added a solution of sodium nitrite (208 mg, 3.01 mmol, 1 .00 eq) in water (0.60 mL) at 0°C. The reaction was stirred at 0°C for 1 h, then cuprous chloride (477 mg, 4.81 mmol, 1 .60 eq) was added at 0°C. The reaction was stirred at 20°C for 1 1 h. Water (50.0 mL) was added, followed by potassium carbonate until pH = 7: The mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (50.0 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 1 /0 to 10/1 ) to afford 1 -chloro-2,4- dimethyl-5-nitrobenzene (400 mg, 2.16 mmol, 72% yield) as a yellow solid.

References:

WO2021/69705,2021,A1 Location in patent:Page/Page column 165

1481-68-1 Synthesis