Decylbenzene → 1,4-Dibromo-2,5-bis((4-decylphenyl)carbonyl)benzene

Participants

Reaction Conditions

Reaction Steps

Compound 7 (19.2 g, 0.059 mol) was dissolved in 100 mL of dry CH2Cl2, and aluminum chloride (16.6 g, 0.12 mol) was added. The reaction turned orange and some precipitate formed. The reaction was cooled to 0° C., and phenyldecane (45.3 g, 0.21 mol) in 50 mL of dry CH2Cl2 was added through an additional funnel. The reaction was stirred at room temperature under nitrogen overnight. The reaction was quenched carefully with 1 N HCl, extracted with CH2Cl2, and the combined organic phase was dried over MgSO4. The crude product was obtained as off-white solid and was recrystallized from acetone to give 31.8 g of pure product as white crystals at 74% yield. 1H NMR (CDCl3) δ (ppm): 0.88 (t, J=6.7 Hz, 6H), 1.26-1.32 (m, 28H), 1.62-1.67 (m, 4H), 2.69 (t, J=7.6 Hz, 4H), 7.32 (d, J=7.9 Hz, 4H), 7.58 (s, 2H), 7.76 (d, J=7.9 Hz, 4H). Mp 128-129° C.

Provenance & Evidence