Hexane → HCID 15594786, compound

HRID 986645Notes

Reaction equation

HRID 986645 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.CCCCCC.C(OCC)(=O)C>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

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 15594784HCID 15594784, compound

Product 1

HCID 15594786HCID 15594786, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

After 9.0 g of (Z)-ethyl 2-fluorocrotonate was dissolved in 60 ml of carbon tetrachloride, 13.5 g of N-bromosuccinimide and 10 mg of benzoyl peroxide were added thereto. The mixture was heated to reflux for 6 hours. This reaction solution was filtered and the filtrate was concentrated to give a residue. The residue was subjected to silica gel column chromatography (eluent; n-hexane:ethyl acetate=20:1), thereby obtaining 8.5 g of the desired compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. filtrationThis reaction solution was filtered
  4. concentrationthe filtrate was concentrated
  5. customto give a residue

Sources & evidence

ORD record
ord-392b6fe082cb4279bcd7d23613efa7a5
Source dataset
uspto-grants-1987_12
Patent number
US04714712

Reaction notes

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