Azobisisobutyronitrile → HCID 11405306, compound

HRID 381676Notes

Reaction equation

HRID 381676 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][CH2:19][CH3:20])=[CH:17][C:11]2=[N:10]1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:33]Br>C(Cl)(Cl)(Cl)Cl>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:33])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[CH:17][C:11]2=[N:10]1

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 24408BromineHCID 11414528HCID 11414528, compound3×

Product 1

HCID 11405306HCID 11405306, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

2-(2′-hydroxy-5′-bromomethyphenyl)-5-ethoxybenzotriazole was prepared from the bromination of 2-(2′-hydroxy-5′-methyphenyl)-5-ethoxybenzotriazole using azobis isobutyronitrile (AIBN) as an initiator. In a 500 ml three-necked round bottomed flask, 6.275 g (0.0223 mol) 2-(2′-hydroxy-5′-methyphenyl)-5-ethoxybenzotriazole 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-ethoxybenzotriazole 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. Produce was separated by solvent evaporation Finally the product was purified by recrystallization from acetone. The yield of 2-(2′-hydroxy-5′-bromomethyphenyl)-5-ethoxybenzotriazole was 6.6 g (85%)

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. customProduce
  9. customwas separated by solvent evaporation Finally the product
  10. customwas purified by recrystallization from acetone

Sources & evidence

ORD record
ord-4b2b1478ad284c9faf88ec699cbed072
Source dataset
uspto-grants-2001_10
Patent number
US06307055B1

Reaction notes

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