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| Typical applications of Bredereck's reagent（CAS:5815-08-7）（5） |
| 2022-06-19 |
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A mixture of 2-methyl-4-nitrobenzonitrile (Aldrich, 5.0 g, 31 mmol) and 1-(1,1-dimethylethoxy)-N,N,N',N'-tetramethyl-methanediamine (12.2 mL, 59 mmol) in dry DMF (8 mL) was stirred at 70° C. for 2 h under N2.
After cooling to rt, DMF was removed in vacuo and the crude product was triturated with hexanes/ethyl acetate (5:1).
The solid was collected by filtration and washed with hexane to give (E)-2-(2-(dimethylamino)vinyl)-4-nitrobenzonitrile (6.5 g, 97% yield) as a black solid.
1H NMR (400 MHz, CDCl3) δ ppm 2.97 (s, 6H) 5.36 (d, J=13.18 Hz, 1H) 7.16 (d, J=13.62 Hz, 1H) 7.52 (d, J=8.79 Hz, 1H) 7.60 (m, 1H) 8.11 (d, J=1.76 Hz, 1H).
Ref : US2006/211720, 2006, A1
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