Acetic Acid → 9-Iodo-10-phenylanthracene

HRID 1639480Notes

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

Conditions

Temperature: 70 °C

Procedure

Into a 500 mL Erlenmeyer flask was put 4.5 g (18 mmol) of 9-phenylanthracene. Then 200 mL of acetic acid was added to the flask, followed by heating to 70° C., and 9-phenylanthracene was dissolved therein. Into this solution, 5.2 g (13 mmol) of 1,3-diiodo-5,5-dimethylimidazolidine-2,4-dione (abbreviation: DIH) was added. This solution was stirred in air at 70° C. for 3 hours. After the stirring, about 100 mL of water and about 200 mL of chloroform were added to this solution. This mixture was washed with water twice, and the aqueous layer was extracted with chloroform. The extracted solution was combined with the organic layer and washed with a saturated saline, and then the organic layer was dried with magnesium sulfate. This mixture was gravity filtered, and the obtained filtrate was concentrated to give a brown solid. This solid was washed with hexane to give 5.8 g of a yellow solid, which was the object of the synthesis, in a yield of 86%.

Workup

washThis mixture was washed with water twice
extractionthe aqueous layer was extracted with chloroform
washwashed with a saturated saline
dry with materialthe organic layer was dried with magnesium sulfate
filtrationfiltered
concentrationthe obtained filtrate was concentrated
customto give a brown solid
washThis solid was washed with hexane

Sources & evidence

ORD record: ord-cfd10bd3bcdd438b8b4b53fa7c79eee2
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110122B2

Reaction notes

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