Benzoyl Peroxide → 1-(Bromomethyl)-4-isothiocyanatobenzene

HRID 1008748Notes

Reaction equation

HRID 1008748 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:27]1([CH3:36])[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[S:35])=[CH:29][CH:28]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:36][C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[S:35])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 12149p-Tolyl isothiocyanateHCID 67184N-bromobutanimide

Product 1

HCID 102428621-(Bromomethyl)-4-isothiocyanatobenzeneYield 63.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-bromosuccinimide (6.26 g) (supplied from Tokyo Chemical Industry) and 1.13 g of 70% benzoyl peroxide (supplied from Aldrich) were added to a solution of 5.02 g of p-tolyl isothiocyanate (supplied from Tokyo Chemical Industry) in 100 mL of carbon tetrachloride, and stirred with heating reflux for 19 hours. The reaction suspension was filtrated and the filtrate was concentrated. The residue was applied onto the silica gel column and eluted with hexane, to yield 4.85 g of the title compound.

Workup

  1. temperaturewith heating
  2. temperaturereflux for 19 hours
  3. filtrationThe reaction suspension was filtrated
  4. concentrationthe filtrate was concentrated
  5. washeluted with hexane

Sources & evidence

ORD record
ord-2cfb6712b1564df6975d3b5cf9671e05
Source dataset
uspto-grants-2011_07
Patent number
US07973030B2

Reaction notes

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