Benzoyl Peroxide → HCID 21999887, compound

HRID 1975943Notes

Reaction equation

HRID 1975943 reaction equation
[F:1][CH:2]([F:15])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][C:5]=1[CH3:14].C1C(=O)N([Br:23])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:15][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][C:5]=1[CH2:14][Br:23]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21999885HCID 21999885, compound

Product 1

HCID 21999887HCID 21999887, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of sulfone 15 from above (0.92 g) dissolved in CCl4 (20 mL) was added NBS (0.83 g) and a catalytic amount of benzoyl peroxide and the resulting mixture was irradiated with a sum lamp under reflux for 4 hours. After cooling to room temperature, the solid was filtered off and the filtrate was concentrated. The crude product was purified by silica gel chromatography. Eluting with ethyl acetate/hexanes (1:5) furnished 2-difluoromethoxy-5-methanesulfonylbenzyl bromide.

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationthe solid was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by silica gel chromatography
  5. washEluting with ethyl acetate/hexanes (1:5)

Sources & evidence

ORD record
ord-336c4c1c44864edf9bf03b211610732e
Source dataset
uspto-grants-2001_05
Patent number
US06225288B1

Reaction notes

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