Benzoyl Peroxide → HCID 54208606, compound

HRID 648991Notes

Reaction equation

HRID 648991 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:15])=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:15][C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 3725577HCID 3725577, compound

Product 1

HCID 54208606HCID 54208606, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 3-(4-fluorophenyl)-2-butenoate (548 g, 2.7 mol), N-bromosuccinimide (500 g, 2.8 mol) and benzoyl peroxide (6 g) are combined in carbon tetrachloride (4 L). The mixture is heated at reflux and irradiated with a UV lamp for 4 days. The mixture is then filtered and the filtrate evaporated, and the residue is dissolved in ether and washed five times with saturated aqueous sodium carbonate and once with brine. The ether layer is dried with magnesium sulfate and evaporated, to provide the title compound.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux
  3. customirradiated with a UV lamp for 4 days
  4. filtrationThe mixture is then filtered
  5. customthe filtrate evaporated
  6. dissolutionthe residue is dissolved in ether
  7. washwashed five times with saturated aqueous sodium carbonate
  8. dry with materialThe ether layer is dried with magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-cb783a466e46416abd1b6ce62ff68dc4
Source dataset
uspto-grants-1988_04
Patent number
US04737511

Reaction notes

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