Benzoyl Peroxide → 2-(Benzenesulfonyl)-3-[4-(bromomethyl)phenyl]prop-2-enenitrile

HRID 1414170Notes

Reaction equation

HRID 1414170 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([CH:7]=[C:8]([C:18]#[N:19])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:3][CH:2]=1.[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:20][C:1]1[CH:2]=[CH:3][C:4]([CH:7]=[C:8]([C:18]#[N:19])[S:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5067622HCID 5067622, compound

Product 1

HCID 542386662-(Benzenesulfonyl)-3-[4-(bromomethyl)phenyl]prop-2-enenitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

56.8 g (0.2 mole) of 1-p-tolyl-2-cyano-2-phenylsulfonylethylene were dissolved in 1.000 ml of anhydrous carbon tetrachloride at 40° to 50° C. After addition of 35.6 g (0.2 mole) of N-bromosuccinimide and 1.2 g of dibenzoylperoxide, the whole was heated to the boil under reflux. After 5 hours, the mixture was filtered by still hot; as residue 17.2 g (about 86%) of succinimide melting at 125° C remained behind. The filtrate was evaporated on a rotary steamer and under the vacuum produced by a water jet and the residue was recrystallized from 400 ml of ethanol. 47.4 g (65 of the theory) of weakly yellow crystal melting at 120° to 122° C were isolated. Characteristical NMR-signal in CDCl3 /TMS: --CH2Br at δ = 4.6 ppm. ##STR15##

Workup

  1. temperaturethe whole was heated to the boil
  2. temperatureunder reflux
  3. filtrationthe mixture was filtered by still hot
  4. customThe filtrate was evaporated on a rotary steamer and under the vacuum
  5. customproduced by a water jet
  6. customthe residue was recrystallized from 400 ml of ethanol

Sources & evidence

ORD record
ord-7978c614ed0546739c76a83be3123ae4
Source dataset
uspto-grants-1977_01
Patent number
US04001221

Reaction notes

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