4-Fluorophenol → 1-(4-Fluorophenoxy)-3-methylbenzene

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (1 80 g) was suspended in 3-bromotoluene (51.3 g, Aldrich) and 4-fluorophenol (8.40 g, Aldrich) added over 1/4 hour with stirring. The mixture was then heated at 45° C. until effervescence stopped (1/2 hour). After cooling, copper(I) chloride (3.75 g) was added followed by TDA-1 (12 g) over 10 minutes with further cooling. The mixture was then heated at 180° C. under N2 for 24 hours. After cooling, the mixture was treated with 2 M aqu. HCl (100 ml) and extracted with ether. The extract was washed with 2 M aqu. HCl (2×100 ml), with 2 M aqu. NaOH and with water (2×100 ml), then treated with charcoal, filtered through Hyflo and stripped. The residue was distilled under reduced pressure to give the desired product, bp 130°-135° C./10 mm Hg.

Provenance & Evidence