Azobisisobutyronitrile → 2-(2'-Hydroxy-3'-tert-butyl-5'-bromomethyphenyl)benzotriazole

HRID 1594999ノート

反応式

HRID 1594999 の反応式
[OH:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][C:5]([CH3:12])=[CH:4][C:3]=1[N:13]1[N:17]=[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]2=[N:14]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[C:7]([C:8]([CH3:9])([CH3:11])[CH3:10])=[CH:6][C:5]([CH2:12][Br:34])=[CH:4][C:3]=1[N:13]1[N:17]=[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]2=[N:14]1

参加物

5

反応物 3

HCID 6547Azobisisobutyronitrile2 回HCID 24408BromineHCID 155678932-(2'-Hydroxy-3'-tert-butyl-5'-methyphenyl)benzotriazole3 回

生成物 1

HCID 155381122-(2'-Hydroxy-3'-tert-butyl-5'-bromomethyphenyl)benzotriazole

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒2 回

実験手順

2-(2′-hydroxy-3′-tert-butyl-5′-bromomethyphenyl)benzotriazole was prepared from the bromination of 2-(2′-hydroxy-3′-tert-butyl-5′-methyphenyl)benzotriazole 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-3′-tert-butyl-5′-methyphenyl)benzotriazole 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-3′-tert-butyl-5′-methyphenyl)benzotriazole 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-3′-tert-butyl-5′-bromomethyphenyl)benzotriazole was 6.6 g (82%)

後処理

  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

出典と根拠

ORDレコード
ord-7bcd0e14dadf49448ac0d278e7841f01
出典データセット
uspto-grants-2001_09
特許番号
US06284895B1

反応ノート

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