Benzoyl Peroxide → HCID 22731428, compound

HRID 2085554Notes

Reaction equation

HRID 2085554 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH3:12])[CH:8]=[CH:9][C:10]=1[F:11])([CH3:4])([CH3:3])[CH3:2].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][C:10]=1[F:11])[CH2:12][Br:13])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22731437HCID 22731437, compound

Product 1

HCID 22731428HCID 22731428, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3-tert-butyl-4-fluorotoluene (5.92 g, 34.4 mmol) in carbon tetrachloride (60 ml), N-bromosuccinimide (6.1 g, 34.4 mmol) and benzoyl peroxide (containing 25% of water) (1.1 g, 3.44 mmol) were added, followed by stirring for 30 min. while heating under reflux. The mixture was evaporated to remove the solvent; the thus obtained residue was mixed with n-hexane and filtered to remove the insoluble matter. The filtrate was evaporated to remove the solvent; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: n-hexane) to give the titled compound (7.01 g, 83%).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. customThe mixture was evaporated
  4. customto remove the solvent
  5. additionthe thus obtained residue was mixed with n-hexane
  6. filtrationfiltered
  7. customto remove the insoluble matter
  8. customThe filtrate was evaporated
  9. customto remove the solvent

Sources & evidence

ORD record
ord-2ad4b5454fdc42a58bb29da0fc8a7b27
Source dataset
uspto-grants-2004_04
Patent number
US06720433B2

Reaction notes

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