Thionyl Chloride → 8-Bromo-7-fluoro-2,3,4,5-tetrahydro-3,5-methano-1H-2-benzazepin-1-one
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[CH:8]1[CH2:13][CH:6]([CH2:7]1)[C:5]2=[N:14]O.S(Cl)(Cl)=[O:17]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([CH:8]3[CH2:13][CH:6]([NH:14][C:5]2=[O:17])[CH2:7]3)=[CH:10][C:11]=1[F:12]Komponenten
4
Versuchsvorschrift
Into a 100-mL round-bottom flask was placed a solution of 6-Bromo-7-fluoro-2,3-dihydro-1H-1,3-methano-naphthalen-4-one oxime (3.5 g, 12.96 mmol, 1.00 equiv) in 1,4-dioxane (30 mL) and thionyl chloride (24.7 g, 207.56 mmol, 16.00 equiv). The resulting solution was heated to reflux for 6 h, cooled, concentrated under vacuum, and quenched by the addition of 50 mL of water/ice. The solids were collected by filtration, washed with 2×50 mL of saturated aqueous NaHCO3 and 2×50 mL of water to afford 3.1 g (89%) of 5-bromo-4-fluoro-9-azatricyclo[8.1.1.0[2,7]]dodeca-2,4,6-trien-8-one as a white solid.