N-bromobutanimide → HCID 15594786, compound

HRID 326797Notes

Reaction equation

HRID 326797 reaction equation
[F:1]/[C:2](=[CH:8]\[CH3:9])/[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:10][CH2:9]/[CH:8]=[C:2](\[F:1])/[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 15594784HCID 15594784, compound

Product 1

HCID 15594786HCID 15594786, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 2-fluorocrotonate (6.0 g) (prepared according to E. D. Bergmann and I. Shahak, J.Chem.Soc., 4033, 1961) N-bromosuccinimide (8.1 g) and benzoyl peroxide (0.15 g) was dissolved in carbon tetrachloride (120 ml) and heated at reflux for 3-5 hours. The mixture was cooled, filtered and the filtrate evaporated to dryness under reduced pressure. Chromatography on silica eluting with 10% diethyl ether: hexane gave ethyl 4-bromo-2-fluorocrotonate as a yellow oil (7.6 g). NMR 1H: 1.5(3H,t), 4.1(2H,dd), 4.4(2H,q), 6.4(1H,dt).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3-5 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ea175f0f3e3f4062bbe113ec49ad9eba
Source dataset
uspto-grants-1993_12
Patent number
US05270343

Reaction notes

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