Iodine → HCID 21531692, compound

HRID 1657919Notes

Reaction equation

HRID 1657919 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][Cl:7])=[CH:4][C:3]=1[CH2:10][CH3:11].II.[Cl:14]Cl>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([CH2:10][CH3:11])=[CH:4][C:5]([CH2:6][Cl:7])=[CH:8][C:9]=1[Cl:14]

Participants

5

Reactant 3

HCID 807IodineHCID 24526ChlorineHCID 21532029HCID 21532029, compound

Product 1

HCID 21531692HCID 21531692, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 46 parts of 4-bromo-3-ethylbenzyl chloride and 3 parts of iodine in 300 parts of chloroform is added 16 parts of chlorine. The solution is refluxed in the absence of light for 6 hours, then cooled and extracted with water and dilute sodium bisulfite solution. The organic phase is separated, dried and concentrated. The residue is chromatographed on Florisil or alumina and 4-bromo-2-chloro-5-ethylbenzyl chloride, 4-bromo-2-chloro-3-ethylbenzyl chloride, and a small amount of 4-bromo-3-chloro-5-ethylbenzyl chloride are isolated as three of the fractions.

Workup

  1. temperatureThe solution is refluxed in the absence of light for 6 hours
  2. temperaturecooled
  3. extractionextracted with water and dilute sodium bisulfite solution
  4. customThe organic phase is separated
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is chromatographed on Florisil or alumina and 4-bromo-2-chloro-5-ethylbenzyl chloride, 4-bromo-2-chloro-3-ethylbenzyl chloride

Sources & evidence

ORD record
ord-e075778599cc4e678c4097df0ec93908
Source dataset
uspto-grants-1976_06
Patent number
US03962307

Reaction notes

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