N-bromobutanimide → 3-Buten-2-one, 3-bromo-4-ethoxy-1,1,1-trifluoro-

HRID 2352414Notes

Reaction equation

HRID 2352414 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][CH:12]=[CH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH3:10]>ClC(Cl)(Cl)Cl>[Br:1][C:13](=[CH:12][O:11][CH2:9][CH3:10])[C:14](=[O:19])[C:15]([F:17])([F:18])[F:16]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27803954-Ethoxy-1,1,1-trifluoro-3-buten-2-one

Product 1

HCID 37290783-Buten-2-one, 3-bromo-4-ethoxy-1,1,1-trifluoro-Yield 78.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

9.8 g (0.055 mole) of N-bromosuccinimide and 100 mg azoisobutyronitrile are added to a solution of 8.4 g (0.05 mole) of 4-ethoxy-1,1,1-trifluoro-but-3-en-2-one in 50 ml of tetrachloromethane. The mixture is then refluxed for 8 hours, the cooled solution is filtered and the filtrate is concentrated. 13.4 g of a crude product are obtained whiose distillation under reduced pressure gives 9.7 g of 3-bromo-4-ethoxy-1,1,1-trifluorobut-3-en-2-one.

Workup

  1. temperatureThe mixture is then refluxed for 8 hours
  2. filtrationthe cooled solution is filtered
  3. concentrationthe filtrate is concentrated
  4. custom13.4 g of a crude product are obtained whiose
  5. distillationdistillation under reduced pressure

Sources & evidence

ORD record
ord-54d553944886458398a857e74ff03636
Source dataset
uspto-grants-1989_10
Patent number
US04876393

Reaction notes

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