Iodine → Stilbene

HRID 1762858Notes

Reaction equation

HRID 1762858 reaction equation
[Br-].[C:2]1(/[CH:8]=[CH:9]\[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C2C(=O)C3C(=CC=CC=3)C=2CCC1.II>C1CCCCC1>[C:2]1([CH:8]=[CH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 807IodineHCID 12461PhentydroneHCID 86743077HCID 86743077, compound

Product 1

HCID 11502Stilbene

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

3.3 g. (0.01 mole) cis-stilbene bromide are dissolved in 100 ml. anhydrous 1,2,3,4-tetrahydro-9-fluorenone. This solution is diluted with 1200 ml. anhydrous cyclohexane and mixed with 1.7 g. iodine. The solution is illuminated, while passing in nitrogen, with a laboratory immersion lamp with cooling tube of the type TQ 150 (Hanau) for 12 to 14 days. The reaction is monitored by thin layer chromatography (dichloromethane/petroleum ether (b.p. 30° to 50° C.) 1:2 v/v). The organic phase is shaken out three times with 300 ml. amounts of thiosulphate solution in order to remove excess iodine. After drying over anhydrous magnesium sulphate, the organic phase is evaporated on a rotary evaporator and the crude product obtained is recrystallised from petroleum ether (b.p. 60° to 90° C.). Yield 1.55 g. (47% of theory).

Workup

  1. additionThis solution is diluted with 1200 ml
  2. customThe solution is illuminated
  3. temperaturewith cooling tube of the type TQ 150 (Hanau) for 12 to 14 days
  4. customamounts of thiosulphate solution in order to remove excess iodine
  5. dry with materialAfter drying over anhydrous magnesium sulphate
  6. customthe organic phase is evaporated on a rotary evaporator

Sources & evidence

ORD record
ord-f71ed719612042cd882d4cfff62f30d2
Source dataset
uspto-grants-1989_05
Patent number
US04835178

Reaction notes

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