Azobisisobutyronitrile → 2-(2'-Hydroxy-3'-tert-butyl-5'-bromomethylphenyl)-5-chlorobenzotriazole

HRID 354218

반응식

HRID 354218 반응식
[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][C:20]([Cl:22])=[CH:21][C:15]2=[N:14]1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:35]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:35])=[CH:4][C:3]=1[N:13]1[N:17]=[C:16]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:15]2=[N:14]1

참가 물질

5

반응물 3

HCID 6547Azobisisobutyronitrile2회HCID 24408BromineHCID 62531Tinuvin3회

생성물 1

HCID 155381112-(2'-Hydroxy-3'-tert-butyl-5'-bromomethylphenyl)-5-chlorobenzotriazole

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매2회

실험 절차

2-(2′-Hydroxy-3′-tert-butyl-5′-bromomethylphenyl)-5-chlorobenzotriazole was prepared from the bromination of 2-(2′-Hydroxy-3′-tert-butyl-5′-methylphenyl)-5-chlorobenzotriazole using azobis isobutyronitrile (AIBN) as an initiator. In a 500 ml three-necked round bottomed flask, 7.042 g (0.0273 mole) 2-(2′-Hydroxy-3′-tert-butyl-5′-methylphenyl)-5-chlorobenzotriazole 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 mole) 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′-methylphenyl)-5-chlorobenzotriazole 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′-bromomethylphenyl)-5-chlorobenzotriazole was 7.2 g (81%).

후처리

  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

출처 및 근거

ORD 기록
ord-1aedcc535e61408392fa529b1746b846
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756499B2

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