4-Bromophenol → 2-[2-(4-Bromophenoxy)ethoxy]tetrahydro-2H-pyran

Participants

Reaction Steps

To a solution of 4-bromophenol (1.71 g, 9.91 mmol) in DMSO (40 mL) was added potassium t-butoxide (1.17 g, 10.4 mmol) and the mixture was stirred for 20 mins. Tetrahydro-2-(2-bromoethoxy-2H-pyran (2.18 g, 10.4 mmol) in DMSO (10 mL) was added dropwise and the reaction was stirred for 1 hr. It was then diluted with brine (100 mL) and extracted with ethylacetate (3×100 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, hexanes:ether, 85:15) to afford tetrahydro-2-(2-(4-bromophenoxy)ethoxy)-2H-pyran (2.52 g, 85%) as a colorless oil.

Provenance & Evidence