1-(2,2-DibroMovinyl)-2-nitrobenzene synthesis
- Product Name:1-(2,2-DibroMovinyl)-2-nitrobenzene
- CAS Number:253684-24-1
- Molecular formula:C8H5Br2NO2
- Molecular Weight:306.94
Yield:253684-24-1 97%
Reaction Conditions:
with triphenylphosphine in dichloromethane at 0; for 0.5 h;Corey-Fuchs olefination;
Steps:
2.1.1 General procedure for the synthesis of (2,2-dibromovinyl)-nitroaryls
1-(2,2-dibromovinyl)-2-nitrobenzene: 2-nitrobenzaldehyde (10.00 g, 66.2 mmol) was dissolved in DCM (350 mL). CBr4 (23.04 g, 69.5 mmol) was added and the solution cooled to 0 °C in an ice bath. PPh3 (36.4 g, 139 mmol) was added in several portions, and the solution stirred at 0 °C until the reaction was complete by TLC (30 minutes). Hexanes (350 mL) were added to precipitate P(O)Ph3 and P(O)Br2Ph3, and the solution was vacuum filtered over a pad of silica gel, rinsing with 10% EtOAc (hexanes). The filtrate was collected and solvent removed to yield pure 1-(2,2-dibromovinyl)-2-nitrobenzene (19.80 g, 97%).
References:
Kunzer, Aaron R.;Wendt, Michael D. [Tetrahedron Letters,2011,vol. 52,# 15,p. 1815 - 1818] Location in patent:supporting information; experimental part
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