Azobisisobutyronitrile → HCID 15538114, compound

HRID 354220Notes

Reaction equation

HRID 354220 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:17][C:11]2=[N:10]1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:34]Br>C(Cl)(Cl)(Cl)Cl>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:34])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:17][C:11]2=[N:10]1

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 24408BromineHCID 15538113HCID 15538113, compound3×

Product 1

HCID 15538114HCID 15538114, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

2-(2′-hydroxy-5′-bromomethyphenyl)-5-tert-butylbenzotriazole was prepared from the bromination of 2-(2′-hydroxy-5′-methyphenyl)-5-tert-butylbenzotriazole using azobis isobutyronitrile (AIBN) as an initiator. In a 500 ml three-necked round bottomed flask, 6.274 g (0.0223 mol) 2-(2′-hydroxy-5′-methyphenyl)-5-tert-butylbenzotriazole and 100 mg of AIBN were taken and dissolved in 150 ml of dry carbon tetrachloride. In a separate conical flask 4.18 g (1.5 ml, 0.03 mol) of bromine was dissolved in 75 ml of dry carbon tetrachloride and solution was transferred to a cylindrical funnel with pressure equalizing tube. Three-necked round-bottomed flask containing solution of 2-(2′-hydroxy-5′-methyphenyl)-5-tert-butylbenzotriazole was kept in oil-bath with temperature 50° C. Nitrogen was bubbled through the solution for creating inert atmosphere. Cylindrical funnel containing bromine solution was mounted on the three-necked round-bottomed flask. Solution in the flask was continuously stirred with the help of magnetic stirrer. Bromine solution was added, drop-by-drop, from funnel to the flask for a span of 4-5 hours till all the solution was poured out. After that heating was stopped and the final reaction mixture was allowed to cool at room temperature. Product was separated by solvent evaporation. Finally the product was purified by recrystallization from acetone. The yield of 2-(2′-hydroxy-5′-bromomethyphenyl)-5-tert-butylbenzotriazole was 6.8 g (84%).

Workup

  1. customsolution was transferred to a cylindrical funnel with pressure
  2. customwas kept in oil-bath with temperature 50° C
  3. customNitrogen was bubbled through the solution
  4. additionCylindrical funnel containing bromine solution
  5. additionBromine solution was added
  6. additiondrop-by-drop, from funnel to the flask for a span of 4-5 hours till all the solution was poured out
  7. customthe final reaction mixture
  8. customProduct was separated by solvent evaporation
  9. customFinally the product was purified by recrystallization from acetone

Sources & evidence

ORD record
ord-570da0e80759408aa87dfedd95e5eb09
Source dataset
uspto-grants-2004_06
Patent number
US06756499B2

Reaction notes

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