Pyrrolidine → 1-{(E)-2-[3-(Benzyloxy)-6-bromo-2-nitrophenyl]vinyl}pyrrolidine

Participants

Reaction Steps

1-Benzyloxy-4-bromo-3-methyl-2-nitro-benzene (20 g, 62.1 mmol; Intermediate 81) was dissolved in DMF. DMFDMA (9.93 ml, 74.5 mmol) and pyrrolidine (6.22 ml, 74.5 mmol) was added. The solution was heated at 110° under nitrogen. TLC (EtOAc/Hexane 1/3) indicated that the starting material was consumed after 2 h. The heating was turned off. The reaction mixture was allowed to adopt room temperature, and was left over night. The solution was evaporated and the residue solidified on standing in the refrigerator. 50 mL of methanol was added and the mixture was heated. The solid was partly dissolved. The mixture was allowed to adopt room temperature, and was then filtered. The solid was washed with methanol and dried. Obtained 17 g.

Provenance & Evidence