Hydrogen Peroxide → HCID 86690456, compound

Participants

Reaction Steps

1-Bromo-3,5-dimethoxybenzene (25.5 g, 117.5 mmol) in THF (150 mL) was added to a mixture of magnesium (3.14 g, 129.2 mmol) and iodine (120 mg) in THF (100 mL). The mixture was refluxed for 1 hour after the addition was completed. It was cooled to RT. The resulting light brown solution was transferred to another flask. It was cooled to −78° C. and chlorobis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine (59.3 g, 117.4 mmol) in THF (100 mL) was added dropwise at −78° C. The resulting mixture was stirred at −78° C. for 0.5 h, then slowly warmed up to RT and stirred at RT for 1 hour. To the resulting mixture water (300 mL) was added, then H2O2 (17 mL, 30%) was added dropwise at 0° C. The mixture was stirred for 30 minutes. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (200 mL×2) and CH2Cl2 (200 mL×1). The combined organic layer was washed with brine (200 mL×2), NaHSO3 (200 mL×3) and dried over MgSO4. It was filtered and the solvent was removed. The viscous residue was dissolved in CH2Cl2 (30 mL) and ether (100 mL), then hexane (400 mL) added. The mixture was concentrated to 400 mL under reduced pressure and then seeded. The suspension was stirred for 1.5 hour and the resulting solid was collected by filtration and dried to give the product as a colorless solid (57 g). a second crop (13 g) was collected from the mother liquor. Yield=95.7%. 1H NMR (300 MHz, CDCl3) δ: 7.47 (d, J=12.6 Hz, 4H), 6.83 (dd, J1=12.6 Hz, J2=2.1 Hz, 2H), 6.60 (t, J=2.1 Hz, 2H), 3.78 (s, 6H), 3.68 (s, 6H), 1.35 (s, 36H). 31P NMR (121.5 MHz, CDCl3) δ: 32.9.

Provenance & Evidence