Benzene, 1-cyclopropyl-4-nitro- synthesis
- Product Name:Benzene, 1-cyclopropyl-4-nitro-
- CAS Number:6921-44-4
- Molecular formula:C9H9NO2
- Molecular Weight:163.17
Yield:6921-44-4 99%
Reaction Conditions:
with palladium diacetate;potassium carbonate;tricyclohexylphosphine in water;toluene at 80; for 1 h;
Steps:
2
Method 2: To a solution of 1 -bromo-4-nitrobenzene (4.95 mmol, 1 g), cyclopropylboronic acid (6.43 mmol, 553 mg), palladium acetate (0.198 mmol, 45 mg), tricyclohexyl phosphine (0.445 mmol, 125 mg) and potassium carbonate (16.4 mmol, 3.5 g) was dissolved in Toluene (20mL) and H20 (2 mL) under Argon. The resulting solution was heated for 1 h at 805C. After the reaction mixture was cooled and concentrated in vacuum. The crude product was purified by flash chromatography on silica gel using an elution of 7% ethylacetate in hexanes to afford 1 -cyclopropyl-4-nitrobenzene (800 mg. Yield: 99%). 1 H NMR (400 MHz, CDCI3) δ 8.1 (2H, dd, J = 2 & 6.8 Hz), 7.15 (2H, dd, J = 2 & 6.8 Hz), 1 .99 (1 H, m), 1 .14-1 .1 1 (2H, m), 0.83-080 (2H, m)
References:
WO2013/149997,2013,A1 Location in patent:Page/Page column 41
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