Benzoyl Peroxide → HCID 18439592, compound

HRID 457462Notes

Reaction equation

HRID 457462 reaction equation
[CH3:1][C:2]1[C:11]([F:12])=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:16][S:13]([C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([CH2:1][Br:17])[C:11]=1[F:12])(=[O:14])=[O:15]

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 18439591HCID 18439591, compoundHCID 86600847HCID 86600847, compound

Product 1

HCID 18439592HCID 18439592, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

30.75 g (0.12 mol) of methyl 2-methyl-3-fluoro-4-methylsulfonylbenzoate were introduced in 600 ml of CCl4. 35.5 g (0.2 mol) of N-bromosuccinimide and 0.86 g (0.002 mol) of benzoyl peroxide were mixed. A third of the amount is added at RT. Then the batch is heated to reflux and “irradiated”. Over the course of an hour the remaining NBS/benzoyl peroxide mixture is added in portions, followed by stirring under reflux for 2 h more. The batch is allowed to cool and is washed with a 10% strength sodium hydrogen sulfite solution, and dried over MgSO4, and the organic phase is concentrated to completion.

Workup

  1. additionA third of the amount is added at RT
  2. temperatureThen the batch is heated
  3. temperatureto reflux
  4. custom“irradiated”
  5. temperatureunder reflux for 2 h more
  6. temperatureto cool
  7. washis washed with a 10% strength sodium hydrogen sulfite solution
  8. dry with materialdried over MgSO4
  9. concentrationthe organic phase is concentrated to completion

Sources & evidence

ORD record
ord-40ffb911e4bf41788fd68381c4101090
Source dataset
uspto-grants-2007_03
Patent number
US07189679B2

Reaction notes

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