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Typical applications of Bredereck's reagent(CAS:5815-08-7)(7) |
2022-06-20 |
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Methyl (E)-2-[2-(Dimethylamino)vinyl]-4-methoxy-5-nitrobenzoate (12)
A mixture of methyl 4-methoxy-2-methyl-5-nitrobenzoate (11) (3.0 g, 13.32 mmol)
and 1-tert-butoxy-N,N,N′,N′-tetramethylmethanediamine (3.3 mL, 15.99 mmol) was heated at 115 °C (no solvent) for 3.5h.
After cooling to r.t., the mixture was triturated with EtOAc/hexanes (1:6).
The solid compound was collected by filtration and dried to provide of methyl (E)-2-[2-(dimethylamino)vinyl]-4-methoxy-5-nitrobenzoate (12) (3.6 g (96%) as an orange colored solid;
mp 160-163 °C.
Ref: [Synthesis, 2017, vol. 49, # 12, p. 2768 - 2774]
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