Iodine → HCID 53861937, compound

Participants

Reaction Steps

Benzyl 4-bromophenyl ether (13.155 g; 50 mmol), prepared in Example 2, in 20 mL THF was added to Mg turnings (1.17 g; 48 mg-atom) in 20 mL THF. Grignard reagent formation was facilitated by addition of a few drops of EtBr2, one crystal of I2, and heat. This mixture was stirred and heated to reflux for 2 h. 11.54 g (45 mmol) desoxyanisoin was added under reflux as a slurry in 60 mL THF. The resulting mixture was stirred at reflux for 18 h, cooled to room temperature, poured onto 200 g 2N H2SO4 and ice (1:1), and stirred at room temperature until the ice melted. The resulting mixture was placed in a separatory funnel and extracted with 200 mL Et2O. The organic layer was washed with aqueous Na2SO5 (100 mL), and brine (2×100 mL). The combined aqueous layers were extracted with Et2O (50 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to give 19 g of a wine colored oil, which was dissolved in Et2O and refrigerated to precipitate any unreacted deoxyanisoin. After filtration and concentration of the solution, the resulting oil was purified on 60 g flash SiO2 (7:3 petroleum ether-CH2Cl2) to yield 12.4 g (65%) of 1-(4-Benzyloxyphenyl)-2,2-bis(4-methoxyphenyl)ethene as a yellow oil. NMR δ7.41 (s, 5H, O-benzyl C6H5), 7.35 to 6.57 (m, 13H, ArH and C=CH), 5.07 (s, 2H, PhCH2O), 3.78 (s, 1.5H, geminal ring OCH3), 3.77 (s, 1.5H, central ring OCH3), 3.72 (s, 3H, vicinal ring OCH3).

Provenance & Evidence