Iodine → 9-Iodo-10-phenylanthracene

HRID 537593

Reaction equation

HRID 537593 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.CCCCCC>[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

7

Reactant 4

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

Product 1

HCID 149583739-Iodo-10-phenylanthraceneYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

3.33 g (10 mmol) of 9-bromo-10-phenylanthracene was dissolved in 80 mL of tetrahydrofuran (abbreviation: THF), and cooled to −78° C. Then, in a reaction solution thereof, 7.5 mL (12.0 mmol) of n-buthyllithium (abbreviation: n-BuLi) (1.6 mol/L hexane solution) was dropped by a dropping funnel and then stirred for one hour. A solution in which 5 g (20.0 mmol) of iodine dissolved in 20 mL of THF was dropped therein, and the further stirred for 2 hours at −78° C. After reaction, a sodium thiosulfate aqueous solution was added therein and stirred. An organic layer was washed with a sodium thiosulfate aqueous solution and saturated saline, and then dried with magnesium sulfate. The mixture was filtrated naturally, then the filtrate was concentrated, and then recrystallized with ethanol, 3.1 g of 9-iodo-10-phenylanthracene that was a target substance was obtained as a light yellow solid at a yield of 83% (Synthesis scheme (b-3)).

Workup

  1. additionwas dropped
  2. stirringthe further stirred for 2 hours at −78° C
  3. customAfter reaction
  4. stirringstirred
  5. washAn organic layer was washed with a sodium thiosulfate aqueous solution and saturated saline
  6. dry with materialdried with magnesium sulfate
  7. filtrationThe mixture was filtrated naturally
  8. concentrationthe filtrate was concentrated
  9. customrecrystallized with ethanol, 3.1 g of 9-iodo-10-phenylanthracene that
  10. customwas obtained as a light yellow solid at a yield of 83% (Synthesis scheme (b-3))

Sources & evidence

ORD record
ord-c5def690792e40f1b745718d1ddb34ce
Source dataset
uspto-grants-2014_10
Patent number
US08860019B2

Linked notes

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