Nitrogen → HCID 12670251, Verbindung

HRID 61316

Reaktionsgleichung

Reaktionsgleichung von HRID 61316
[Br:1][CH:2]1[C:5]2=[CH:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3]1.N#N.[Br:12]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>ClC1C=CC=CC=1>[Br:1][C:2]1([Br:12])[C:5]2=[CH:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH2:3]1

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5685917-Bromobicyclo[4.2.0]octa-1,3,5-triene

Produkt 1

HCID 12670251HCID 12670251, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Bromobenzocyclobutene (91.5 g, 0.5 mol) and chlorobenzene(anhydrous, 2500 mL) were charged into a four-neck 5 L flask equipped with mechanical stir, condenser, N2 (in and outlet) and thermometer. The reaction mixture was heated to 120° C., and N-bromosuccinimide (111.3 g, 0.625 mol) was gradually charged over 30 min., followed by slowly feeding a mixture of a free radical azo compound source (VAZO™ 68) (14.0 g, 0.05 mol) and chlorobenzene (500 mL) over 30 min. Then the reaction mixture was heated to 133° C. (mild reflux) and kept at that temperature for 6 hr. The mixture was then cooled to room temperature overnight, and chlorobenzene was removed by vacuum evaporation. The crude product was extracted with hexane. After removal of hexane, 1-bromo-bromobenzocyclobutene (1-Br-BrBCB) (80-85° C/0.35 torr, 90 g, ca. 93% purity) was obtained by vacuum distillation.

Aufarbeitung

  1. temperatureThen the reaction mixture was heated to 133° C.
  2. temperature(mild reflux)
  3. temperatureThe mixture was then cooled to room temperature overnight
  4. customchlorobenzene was removed by vacuum evaporation
  5. extractionThe crude product was extracted with hexane
  6. customAfter removal of hexane

Quellen und Nachweise

ORD-Eintrag
ord-3899512d2f51492bb1b2c07fddff8478
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441055B1

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