Iodine → 9-Iodo-10-phenylanthracene

HRID 2360745Notes

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

Conditions

Temperature: -78 °C

Procedure

After 3.33 g (10 mmol) of 9-bromo-10-phenylanthracene was dissolved in 80 mL of tetrahydrofuran (abbreviation: THF) and cooled to −78° C., 7.5 mL (12.0 mmol) of n-BuLi (1.6 mol/L) was dripped through a dropping funnel into the reaction solution, and the mixture was stirred for one hour. Subsequently, a solution of 5 g (20.0 mmol) of iodine dissolved in 20 mL of THF was dripped, and the solution was stirred further at −78° C. for 2 hours. After the reaction, a sodium thiosulfate aqueous solution was added to stop the reaction. An organic layer was washed with a sodium thiosulfate aqueous solution and a saturated saline solution and dried with magnesium sulfate. After the solution was filtered naturally, the filtrate was concentrated and recrystallized with ethanol; thus, 3.1 g of a light yellow solid of 9-iodo-10-phenylanthracene that was an object was obtained (yield: 83%).

Workup

stirringthe solution was stirred further at −78° C. for 2 hours
customAfter the reaction
customthe reaction
washAn organic layer was washed with a sodium thiosulfate aqueous solution
dry with materiala saturated saline solution and dried with magnesium sulfate
filtrationAfter the solution was filtered naturally
concentrationthe filtrate was concentrated
customrecrystallized with ethanol
customwas obtained (yield: 83%)

Sources & evidence

ORD record: ord-dea129d7b65d4f42a8aefb6cdaf3a246
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686159B2

Reaction notes

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