9-Iodophenanthrene

Chemical Properties

solid

Synthesis

General procedure for the synthesis of 9-iodophenanthrene from 9-bromophenanthrene: General method: aryl bromide (10 mmol) was dissolved in anhydrous THF (30 mL) and cooled to -78 °C at room temperature. Slowly add n-butyllithium (1.6 M, dissolved in hexane; 7.5 mL; 12 mmol) dropwise. After 15 min of reaction, a solution of anhydrous THF (10 mL) with iodine (I2, 3.81 g; 15 mmol) was added, followed by gradual warming of the reaction mixture to room temperature and stirring overnight. After completion of the reaction, the mixture was concentrated under vacuum. Water (H2O) was added to the residue and extracted with dichloromethane (DCM, 3 times). The organic phases were combined and washed sequentially with saturated sodium thiosulfate (Na2S2O5) solution and water. The organic phase was dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure, and the resulting crude product was purified by column chromatography.

References

[1] Synlett, 2013, vol. 24, # 20, p. 2730 - 2734
[2] Synthesis, 1986, # 1, p. 121 - 122
[3] Journal of Organic Chemistry, 2009, vol. 74, # 12, p. 4650 - 4653
[4] Tetrahedron Letters, 1999, vol. 40, # 36, p. 6671 - 6672
[5] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1499 - 1503