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| Typical applications of Bredereck's reagent（CAS:5815-08-7）（17） |
| 2022-06-21 |
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A mixture of l-tert-butoxy-N,N,N',N'-tetramethylmethanediamine(CAS:5815-08-7) (300 mL,1452.80 mmol) and 2-methyl-6-nitrobenzonitrile (75 g, 462.55 mmol) was heated at 1000C for 4 hours.
The mixture was evaporated and the residue stirred vigorously in isohexane (1500 mL) for 2 hours.
The mixture was filtered and the residue washed with isohexane (2x 500 mL) and then air-dried to afford (E)-2-(2-(dimethylamino)vinyl)-6- nitrobenzonitrile (96g, 95% yield)
; IH NMR spectrum (300 MHz, CDCl3): δ 2.98 (6H, s), 5.52 (IH, d), 7.11 (IH, d), 7.40 (IH, t), 7.60 - 7.70 (2H, m);
Mass spectrum: m/z (ESI+) (M+H)+ = 218.50.
Ref：Synthesis, 2007, # 7, p. 981 - 983
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