2-Bromo-4-fluoronitrobenzene synthesis
- Product Name:2-Bromo-4-fluoronitrobenzene
- CAS Number:700-36-7
- Molecular formula:C6H3BrFNO2
- Molecular Weight:220
371-40-4
700-36-7
General procedure for the synthesis of 1-bromo-5-fluoro-2-nitrobenzene from 4-fluoroaniline: N-bromosuccinimide (34 g, 180 mmol) was dissolved in dichloromethane (60 mL) at 0 °C and slowly added dropwise to a solution of 4-fluoroaniline (20 g, 180 mmol) in dichloromethane (100 mL). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, it was washed sequentially with saturated sodium sulfite solution, saturated sodium bicarbonate solution and brine, and then concentrated to give 1-bromo-5-fluoro-2-nitrobenzene (34 g, 154.5 mmol, 100% yield). The 1H NMR (400 MHz, CDCl3) data of the product were as follows: δ 7.12-7.21 (m, 1H), 7.47 (dd, J = 7.60, 2.40 Hz, 1H), (dd, J = 9.60, 6.40 Hz, 1H).
1003-98-1
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Yield:700-36-7 71%
Reaction Conditions:
with 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane for 10 h;Reflux;
Steps:
General procedure for the oxidation of aromatic amines with m-CPBA:
General procedure: m-CPBA(1.7 g, 8.0 mmol, 85%) was dissolved in 1,2-dichloroethane (15.0 mL) in a threeneckflask equipped with a condenser and heated to reflux (at rt in case of 1b).Then, the substrate aromatic amine (2.0 mmol) dissolved in 1,2-dichloroethane(5.0 mL) was added dropwise to the refluxing peracid solution. After 10 h, themixture was cooled to rt and quenched with saturated aqueous Na2S2O3. Thesolvent was removed under reduced pressure and the residue was treated with10% NaOH solution followed by extraction with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous Na2SO4. Removal of thesolvent under vacuum afforded the crude product, which was purified bycolumn chromatography using hexane/ethyl acetate as eluant.
References:
Liu, Jia;Li, Jue;Ren, Jiangmeng;Zeng, Bu-Bing [Tetrahedron Letters,2014,vol. 55,# 9,p. 1581 - 1584]
371-40-4
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320-98-9
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700-36-7
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1073-06-9
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