Acetic Acid → 9-Iodo-10-phenylanthracene

HRID 2061317Notes

Reaction equation

HRID 2061317 reaction equation
[C:1]1([C:7]2[C:8]3[C:13]([CH:14]=[C:15]4[C:20]=2[CH:19]=[CH:18][CH:17]=[CH:16]4)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[I:25]N1C(C)(C)C(=O)N(I)C1=O.O>C(Cl)(Cl)Cl>[I:25][C:14]1[C:15]2[C:20]([C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:8]3[C:13]=1[CH:12]=[CH:11][CH:10]=[CH:9]3)=[CH:19][CH:18]=[CH:17][CH:16]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 117669-Phenylanthracene2×HCID 2005341,3-Diiodo-5,5-dimethylimidazolidine-2,4-dione

Product 1

HCID 149583739-Iodo-10-phenylanthraceneYield 117.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

In a 500 mL Erlenmeyer flask was added 4.5 g (18 mmol) of 9-phenylanthracene. To the flask was added 200 mL of acetic acid, followed by heating at 70° C. to dissolve 9-phenylanthracene therein. To the resulting solution was added 5.2 g (13 mmol) of 1,3-diiodo-5,5-dimethylimidazolidine-2,4-dione (DIH), and the solution was stirred under air at 70° C. for 3 hours. After the reaction, ca. 100 mL of water and ca. 200 mL, of chloroform were added to this solution. The resulting mixture was washed with water twice, and the organic layer was separated from the aqueous layer. The aqueous layer was extracted with chloroform. The extract was combined with the organic layer and washed with brine, and then the combined organic layer was dried with magnesium sulfate. This mixture was gravity filtered, and the filtrate obtained was concentrated to give a brown solid. This solid was washed with hexane to give 5.8 g of a yellow solid in a yield of 86%, which was the desired substance. The synthetic scheme is shown in the following (A-2).

Workup

  1. washThe resulting mixture was washed with water twice
  2. customthe organic layer was separated from the aqueous layer
  3. extractionThe aqueous layer was extracted with chloroform
  4. washwashed with brine
  5. dry with materialthe combined organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate obtained
  8. concentrationwas concentrated
  9. customto give a brown solid
  10. washThis solid was washed with hexane

Sources & evidence

ORD record
ord-910e6152605e49d6ba28dc5df7b61bda
Source dataset
uspto-grants-2012_10
Patent number
US08283055B2

Reaction notes

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