Azobisisobutyronitrile → 1-[2-(Bromomethyl)-3,3-dimethylbut-1-en-1-yl]-2,4-dichlorobenzene

HRID 649518Notes

Reaction equation

HRID 649518 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[C:10]([CH3:15])[C:11]([CH3:14])([CH3:13])[CH3:12].[Br:16]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>ClC(Cl)C(Cl)Cl>[Br:16][CH2:15][C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 53767202HCID 53767202, compound

Product 1

HCID 545259841-[2-(Bromomethyl)-3,3-dimethylbut-1-en-1-yl]-2,4-dichlorobenzeneYield 62.1%

Reagents, catalysts & solvents 1

HCID 65911,1,2,2-TetrachloroethaneSolvent

Procedure

A mixture of 24.3 g (0.1 mol) of 1-(2,4-dichlorophenyl)-2,3,3-trimethylbut-1-ene, 17.8 g (0.1 mol) of N-bromosuccinimide and a spatula-tip of azodiisobutyrodinitrile in 100 ml of absolute 1,1,2,2-tetrachloroethane is boiled under reflux overnight. For working up, the mixture is concentrated in vacuo, the residue is taken up in carbon tetrachloride, the mixture is filtered and the filtrate is distilled. 20 g (62.1% of theory) of 2-bromomethyl-1-(2,4-dichlorophenyl)-3,3-dimethylbut-1-ene of boiling point 108° C. at 0.13 mbar are obtained. ##STR100##

Workup

  1. temperatureunder reflux overnight
  2. concentrationthe mixture is concentrated in vacuo
  3. filtrationthe mixture is filtered
  4. distillationthe filtrate is distilled

Sources & evidence

ORD record
ord-29adf584186d4acdb001ab9105ae1cfa
Source dataset
uspto-grants-1988_04
Patent number
US04740515

Reaction notes

Loading…