Azobisisobutyronitrile → ethyl (E)-4-bromo-3-phenylbut-2-enoate

HRID 16648

Reaction equation

HRID 16648 reaction equation
[C:1]1(/[C:7](/[CH3:14])=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:27]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:14]/[C:7](/[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5354836Ethyl (2E)-3-phenyl-2-butenoate

Product 1

HCID 13928128ethyl (E)-4-bromo-3-phenylbut-2-enoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 14 g (74 mmol) of ethyl (E)-3-phenylbut-2-enoate, 0.47 g of 2,2′-azobis(2-methylpropionitrile) and 330 ml of carbon tetrachloride is heated to 75° C. 19.8 g (111 mmol) of N-bromosuccinimide are added portionwise at this temperature. The mixture is then refluxed for five hours. The insoluble material is filtered off at 25° C. The filtrate is washed with water and dried over Na2SO4; the solvents are evaporated off (orange-coloured oil: 19.7 g; 99%).

Workup

  1. temperatureThe mixture is then refluxed for five hours
  2. filtrationThe insoluble material is filtered off at 25° C
  3. washThe filtrate is washed with water
  4. dry with materialdried over Na2SO4
  5. customthe solvents are evaporated off (orange-coloured oil: 19.7 g; 99%)

Sources & evidence

ORD record
ord-33c95e91bcc34572aa32018660fd2a43
Source dataset
uspto-grants-2010_06
Patent number
US07737176B2

Linked notes

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