Iodine → HCID 67327154, compound

Participants

Reaction Conditions

Reaction Steps

To a THF (40 mL) solution of 2-(4-bromo-2-fluorophenyl)-1,3-dioxolane (3.29 g) was added Mg (406 mg) and I2 (135 mg), then the resultant mixture was refluxed for 5 hours. After cooling to 0° C., the reaction mixture was added ethylene oxide (12.5 mL, 1.1 M in THF), then the resultant mixture was stirred at 50° C. for 3 hours. The reaction mixture was added ethylene oxide (12.5 mL, 1.1 M in THF), the resultant mixture was stirred at 50° C. over night. The mixture was poured into saturated aqueous NH4Cl, and extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=99/1 to 4/1) to afford a colorless oil. To a THF (10 mL) solution of that colorless oil and PPh3 (857 mg) and alpha,alpha,alpha-trifluoro-p-cresol (530 mg) were added DEAD (1.486 mL, 2.2 M in toluene) at 0° C., then the resultant mixture was stirred at room temperature over night. The reaction mixture was evaporated, to the residue was added n-hexane/AcOEt (4/1), then the mixture was filtered, and the filtrate was evaporated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/0 to 9/1) to afford 2-(2-fluoro-4-{2-[4-(trifluoromethyl)phenoxy]ethyl}phenyl)-1,3-dioxolane as a colorless oil (0.552 g).

Provenance & Evidence