Iodine → HCID 13338730, compound

HRID 485668Notes

Reaction equation

HRID 485668 reaction equation
[NH:1]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:14].P(Cl)(Cl)(Cl)(Cl)Cl.II.[Br:23]Br>C(Cl)(Cl)Cl>[Br:23][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:1][C:2]1=[O:14]

Participants

6

Reactant 4

HCID 807IodineHCID 24408BromineHCID 24819Phosphorus pentachlorideHCID 13338729HCID 13338729, compound

Product 1

HCID 13338730HCID 13338730, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1,3,4,5,6,7-hexahydro-1-benzazonin-2-one (4.7 g) in chloroform (75 ml), phosphorus pentachloride (5.9 g) is added in portions, while maintaining the temperature at 0°-5°. When addition is complete, iodine (60 mg) is added, followed by bromine (4.5 g), which is added dropwise over five minutes. The mixture is then refluxed for 4 hours. The chloroform solution is evaporated and the residue partitioned between ice/water (60 ml) and dichloromethane (100 ml). The organic phase is dried over magnesium sulfate and evaporated under reduced pressure. The crude residue is purified by chromatography on silica gel, eluting with ether/hexane mixtures. Concentration of the appropriate fractions yields 3-bromo-1,3,4,5,6,7-hexahydro-1-benzazonin-2-one.

Workup

  1. temperaturewhile maintaining the temperature at 0°-5°
  2. additionWhen addition
  3. additionis added dropwise over five minutes
  4. temperatureThe mixture is then refluxed for 4 hours
  5. customThe chloroform solution is evaporated
  6. customthe residue partitioned between ice/water (60 ml) and dichloromethane (100 ml)
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe crude residue is purified by chromatography on silica gel
  10. washeluting with ether/hexane mixtures

Sources & evidence

ORD record
ord-d13b477ee9014589aa7f10d0efd43823
Source dataset
uspto-grants-1985_08
Patent number
US04537885

Reaction notes

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