Azobisisobutyronitrile → HCID 15539135, compound

HRID 429993Notes

Reaction equation

HRID 429993 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]([O:18][CH3:19])=[CH:17][C:11]2=[N:10]1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:32]Br>C(Cl)(Cl)(Cl)Cl>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:32])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:11]2=[N:10]1

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 24408BromineHCID 15538117HCID 15538117, compound3×

Product 1

HCID 15539135HCID 15539135, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

2-(2′-hydroxy-5′-bromomethyphenyl)-5-methoxybenzotriazole was prepared from the bromination of 2-(2′-hydroxy-5′-methyphenyl)-5-methoxybenzotriazole using azobis isobutyronitrile (AIBN) as an initiator. In a 500 ml three-necked round bottomed flask, 5.693 g (0.0223 mol)2-(2′-hydroxy-5′-methyphenyl)-5-methoxybenzotriazole 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-methoxybenzotriazole 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 tunnel 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-methoxybenzotriazole was 6.3 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 tunnel 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-46d408e2757c451fa3580b8ec36d743e
Source dataset
uspto-grants-2001_11
Patent number
US06320056B1

Reaction notes

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