Benzoyl Peroxide → HCID 57655944, compound

HRID 911452Notes

Reaction equation

HRID 911452 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:10][C:11]([CH3:20])([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])=[O:9])=[CH:4][CH:3]=1.C1C(=O)N([Br:28])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.O>[Br:28][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:10][C:11]([CH3:20])([C:16]([F:19])([F:17])[F:18])[C:12]([F:13])([F:14])[F:15])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 57656139HCID 57656139, compound

Product 1

HCID 57655944HCID 57655944, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To 1-methyl-4-(3,3,3-trifluoro-2-methyl-2-trifluoromethylpropane-1-sulfinyl)-benzene (4.13 g, 13.0 mmol) in carbon tetrachloride (50 mL) add NBS (2.31 g, 13.0 mmol), benzoyl peroxide (314 mg, 1.30 mmol) and stir overnight at reflux. Cool to ambient temperature, dilute with water and extract three times with EtOAc. Dry over anhydrous Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to give the title compound as colorless oil (2.3 g, 55%).

Workup

  1. temperatureat reflux
  2. extractionextract three times with EtOAc
  3. dry with materialDry over anhydrous Na2SO4
  4. concentrationconcentrate in vacuo
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (9:1)

Sources & evidence

ORD record
ord-9dc09865dcfd493b81e70c351c4ea2d9
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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