Nitrogen → HCID 12670251, compound

HRID 61316

Reaction equation

HRID 61316 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 12670251HCID 12670251, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3899512d2f51492bb1b2c07fddff8478
Source dataset
uspto-grants-2016_09
Patent number
US09441055B1

Linked notes

Loading…