ChemicalBook CAS DataBase List 1-TERT-BUTYL-4-NITROBENZENE

1-TERT-BUTYL-4-NITROBENZENE synthesis

8synthesis methods

Product Name:1-TERT-BUTYL-4-NITROBENZENE
CAS Number:3282-56-2
Molecular formula:C10H13NO2
Molecular Weight:179.22

35779-04-5

3282-56-2

GENERAL STEPS: Add 1-tert-butyl-4-iodobenzene (0.5 mmol), copper(II) trifluoromethanesulfonate (45 mg, 0.125 mmol), potassium nitrite (KNO2, 128 mg, 1.5 mmol), and anhydrous dimethylsulfoxide (DMSO, 0.6 mL) to an oven-dried pressure tube under nitrogen atmosphere. The pressure tube was sealed with a polytetrafluoroethylene screw cap with a microvalve and purged through nitrogen for 5 min to displace the air. The mixture was stirred at room temperature for 10 minutes and then gradually warmed to 130 °C and the reaction was maintained at this temperature for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature, washed with excess ice water and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (Table 2, entries 1-18) or basic alumina column chromatography (Table 2, entries 19-23) using a mixture of ethyl acetate and hexanes as eluent to give 1-tert-butyl-4-nitrobenzene in good final yield.

769-92-6 Synthesis

769-92-6
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3282-56-2
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$11.00/1g

Yield: 90%

Reaction Conditions:

with dihydrogen peroxide;potassium carbonate in water;acetonitrile at 20;

Steps:

I General procedure for the synthesis of substituted nitrobenzenes (2a-z).
General procedure: To a solution of p-toluidine (1.0 mmol) and potassium carbonate (1.0 mmol) in CH₃CN (3 mL) were added a solution of 50% aqueous H₂O₂ (3.0 mmol) and the mixture was stirred at room temerature for 10-15 min. The mixture was then dried to vacuum and extracted three times with ethyl acetate followed by washing with brine,and dried over anhydrous Na₂SO₄. Evaporation of the solvent under vacuum afforded the crude product, which was furthur purified by column chromatography using hexane/ethyl acetate mixture and then analyzed by spectroscopy.

References:

Gupta, Sampa;Ansari, Alisha;Sashidhara, Koneni V. [Tetrahedron Letters,2019,vol. 60,# 39,art. no. 151076] Location in patent:supporting information

35779-04-5 Synthesis

35779-04-5
205 suppliers
$6.00/1g

3282-56-2
78 suppliers
$11.00/1g

References

123324-71-0 Synthesis