Iodine → 9-Iodo-10-phenylanthracene

HRID 2075612Notes

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 dropped 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 dropped, and the solution was further stirred at −78° C. for two 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 saturated saline 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 as a target matter was obtained with a yield of 83%.

Workup

additionwas dropped
stirringthe solution was further stirred at −78° C. for two hours
customAfter the reaction
customthe reaction
washAn organic layer was washed with a sodium thiosulfate aqueous solution and saturated saline
dry with materialdried with magnesium sulfate
filtrationAfter the solution was filtered naturally
concentrationthe filtrate was concentrated
customrecrystallized with ethanol

Sources & evidence

ORD record: ord-d32c3af671e342858e1a7ed35058e50a
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919773B2

Reaction notes

Loading…