Dichloromethane → HCID 71251706, compound

Participants

Reaction Steps

Under nitrogen atmosphere 4.3 grams of 1,1′-(6-methoxy-[1,1′-biphenyl]-3,4′-diyl)bis(2-methylpropan-1-one), which was prepared by following a procedure described in the below Example 4 for the synthesis of (6-methoxy-[1,1′-biphenyl]-3,4′-diyl)bis(phenylmethanone), was mixed with 80 mL of dry dichloromethane and 10 mL of CCl4 at room temperature. 4.2 grams of bromine was added and the resultant solution was continuously stirred at this temperature until the reaction completion was detected by TLC monitoring. The mixture was then concentrated and the residue was mixed with 100 mL of 2N NaOH solution. After stirring overnight the mixture was poured into 200 mL of water, and the aqueous layer was extracted by 100 mL of dichloromethane. The combined organic layer was washed by brine and dried over MgSO4. The filtered solution was then concentrated and the residue was loaded onto silica gel column and eluted by mixtures of hexane/ethyl acetate to give 3.6 grams of the light-yellow product (77% yield). 1H NMR (CDCl3, ppm): 8.13-8.09 (m, 4H), 7.63 (d, 2H, J=8.4 Hz), 7.05 (d, 1H, J=9.0 Hz), 4.17 (s, 1H), 4.16 (s, 1H), 1.68 (s, 6H), 1.65 (s, 6H); 13C NMR (CDCl3, ppm): 204.0, 202.4, 160.2, 142.2, 133.0, 132.3, 129.6, 129.5, 129.2, 126.1, 110.6, 77.4, 76.0, 55.8, 28.6, 28.1.

Provenance & Evidence