Bromine → 6,8-Dibromo-1H-benzo[cd]indol-2-one

HRID 1164319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1164319
[Br:1]Br.[Br:3][C:4]1[C:5]2[C:6]3[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]=3[CH:14]=[CH:15][CH:16]=2>C(O)(=O)C>[Br:3][C:4]1[C:5]2[C:6]3[C:10](=[C:11]([Br:1])[CH:12]=1)[NH:9][C:8](=[O:13])[C:7]=3[CH:14]=[CH:15][CH:16]=2

Komponenten

4

Edukt 2

HCID 24408BromineHCID 7547635-Bromo-8-naphtholactam

Produkt 1

HCID 7548256,8-Dibromo-1H-benzo[cd]indol-2-oneAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

A solution of bromine (3.8 g) in glacial acetic acid (15 mL) was added dropwise to a suspension of 6-bromo-benz[cd]indol-2(1H)-one[4 g, 16.1 mmol, described by H. Goldstein and P. Francey, Helv., 15, 1366 (1932)] in glacial acetic acid (30 mL) for 3-4 hr. The precipitate was collected by filtration, washed, dried (any coloration caused by the excess of bromine could be removed by washing with a diluted sodium thiosulfate solution), and crystallized from ethanol-water to give the title compound (3.5 g): mp 280°-290° C.; Anal. Calcd for C11H5Br2NO: C, 40.41% H, 1.54% N, 4.28% and Found: C, 40.52% H, 1.51% N, 4.43%; IR (mineral oil) 3140 and 1700 cm-1 ; UV max (methanol) 345 (ε4370), 329 (2910), 264 (27,680), and 212 nm (30,920); and NMR (DMSO-d6)δ 8.0 (m, 4H), and 11.3 (s, 1H).

Aufarbeitung

  1. filtrationThe precipitate was collected by filtration
  2. washwashed
  3. customdried (any coloration
  4. customcould be removed
  5. washby washing with a diluted sodium thiosulfate solution), and
  6. customcrystallized from ethanol-water

Quellen und Nachweise

ORD-Eintrag
ord-638937739c454da2b1a2b56a66d9935b
Quelldatensatz
uspto-grants-1983_01
Patentnummer
US04369188

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