ChemicalBook CAS DataBase List 2-Nitrofluorene

2-Nitrofluorene synthesis

9synthesis methods

Product Name:2-Nitrofluorene
CAS Number:607-57-8
Molecular formula:C13H9NO2
Molecular Weight:211.22

86-73-7 Synthesis

86-73-7
399 suppliers
$6.00/25g

607-57-8
168 suppliers
$16.00/5g

Yield:607-57-8 92%

Reaction Conditions:

with nitric acid;acetic acid at 60; for 0.166667 h;

Steps:

2-Nitro-9H-fluorene (3)
9H-Fluorene (6.0 g, 36.1 mmol)was dissolved in 100 mL of glacial acetic acid at 60 °C. 15 mLof nitric acid (65%) were added dropwise (~10 min) at 60 °Cupon vigorous stirring. After the addition was completed, theresulting mixture was further stirred at 60 °C. The reaction wasmonitored by TLC (solvent EtOAc-n-heptane 1:9). After appearance of the spot of the dinitro product (≈100 min, Rf≈25%), the mixture was poured into 600 mL of water. The resulting crude product was filtered off, washed with water andrecrystallized from 200 mL acetonitrile to give compound 3(7.1 g, 92%) as slightly-yellow needles. 1H NMR (CDCl3,400 MHz) δ8.42 (s, 1H), 8.31 (d, J= 8.4 Hz, 1H), 7.89-7.87(m, 2H), 7.64 (d, J= 6.4 Hz, 1H), 7.49-7.43 (m, 2H), 4.02 (s,2H) ppm; 13C NMR (CDCl3, 100 MHz) δ148.09, 146.79,144.81, 143.92, 139.47, 128.87, 127.43, 125.43, 123.14, 121.34,120.49, 119.88, 36.96 ppm.

References:

Hosseinzadeh, Rahman;Nemati, Mohammad;Zadmard, Reza;Mohadjerani, Maryam [Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 1749 - 1757]

FullText