Iodine → 9-Iodo-10-phenylanthracene

HRID 600104Notes

Reaction equation

HRID 600104 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Li]CCCC.[I:27]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[I:27][C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

6

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 41558369-Bromo-10-phenyl-anthraceneHCID 178418339Butyllithium

Product 1

HCID 149583739-Iodo-10-phenylanthraceneYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.33 g (10 mmol) of 9-bromo-10-phenylanthracene was dissolved in 80 ml of tetrahydrofuran (abbrev.: THF). After bringing the temperature to −78° C., 7.5 ml (12.0 mmol) of n-BuLi (1.6M) was added to the reaction solution dropwise with a dropping funnel, and the mixture was stirred for 1 hour. A solution of 5 g (20.0 mmol) of iodine dissolved in 20 ml of THF was added dropwise, and the mixture was stirred for another 2 hours at −78° C. After the reaction, a sodium thiosulfate solution was added and the reaction was stopped. The organic layer was washed with a sodium thiosulfate solution and a saturated saline solution, and dried with magnesium sulfate. After natural filtration, the filtrate was concentrated, and the solid obtained was recrystallized with ethanol. The target substance of 9-iodo-10-phenylanthracene was obtained as a pale yellow solid, weighing 3.1 g in a yield of 83% (synthesis scheme (j-5)).

Workup

  1. customto −78° C.
  2. additionwas added dropwise
  3. stirringthe mixture was stirred for another 2 hours at −78° C
  4. customAfter the reaction
  5. washThe organic layer was washed with a sodium thiosulfate solution
  6. dry with materiala saturated saline solution, and dried with magnesium sulfate
  7. filtrationAfter natural filtration
  8. concentrationthe filtrate was concentrated
  9. customthe solid obtained
  10. customwas recrystallized with ethanol

Sources & evidence

ORD record
ord-9eb26d869aed4652b52b80eba1f14760
Source dataset
uspto-grants-2011_03
Patent number
US07897964B2

Reaction notes

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