Ethylene Glycol → 2-(5-Bromo-2-fluorophenyl)-1,3-dioxolane

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Reaction Steps

5-Bromo-2-fluorobenzaldehyde (14.6 mL, 0.123 mol, Avocado) is combined with 4-methylbenzenesulfonic acid hydrate (2.34 g, 12.0 mmol, Aldrich), ethylene glycol (13.7 mL, 0.25 mol, Mallinkrodt) and toluene (75 mL). The mixture is heated to reflux overnight. The resulting solution is diluted into EtOAc (100 mL) and washed 2× with saturated NaHCO3, 1× with water and 1× with brine (170 mL ea). The organic layer is dried over Na2SO4 and filtered. The solvent is removed by rotary evaporation and the product is purified on a Biotage Flash 75 L (800 g silica) cartridge using 96:3:1 heptane: EtOAc:TEA as eluent.

Provenance & Evidence