Bromobenzene → 2-tert-Butyl-9,10-diphenylanthracene

Participants

Reaction Steps

The bromobenzene (10 g, 63.69 mmol) was placed into a 500 mL round bottom flask under argon which was dissolved into anhydrous THF (150 mL). The reaction was cooled to −78° C. (dry ice/acetone) and the nBuLi (32 mL, 63.69 mmol) was added slowly over 15 minutes. The reaction was stirred for 3 hours while the reaction warmed to room temperature. The reaction was cooled again to −78° C. and the 2-t-butylanthraquinone (5.6 g, 21.23 mmol)(dissolved in 20 mL THF) was added dropwise to the reaction. Once the addition was complete the reaction was allowed to stir at room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride solution and ethyl acetate (100 mL) was added. The aqueous layer was removed and the organic layer was washed twice more with ammonium chloride solution. The organic layer was collected, dried (MgSO4) and conc in vacuo to give a yellow oil which was used directly in the next step. The product was dissolved into 1,4-dioxane (50 mL) and a mixture of 1:1 H2O:AcOH (75 mL) was added. Tin(II) chloride dihydrate (33.48 g, 148.73 mmol) was added and the reaction was heated at 50° C. for 3 hours. The reaction was cooled to room temperature and methanol (50 mL) was added. The reaction mixture was filtered and the precipitate washed with methanol. The solid was collected, dried and was purified by Kaufmann column (alumina, cyclohexane). Further purification was achieved by sublimation (twice) at 260° C. to give >99% purity of 2-tert-butyl-9,10-diphenylanthracene.

Provenance & Evidence