4-Bromophenol → 4-bromophenyl pivalate

Participants

Reaction Steps

A solution of 20.02 g of 4-bromophenol (0.116 mol) in 100 mL of dry THF was treated with 15.0 mL of pivaloyl chloride (0.126 mol), followed by 35.5 mL of triethylamine (0.255 mol). A large amount of white solid precipitated so 50 mL of additional THF was added to the mixture to afford a free-flowing slurry. The reaction mixture was filtered and the precipitate was washed with 200 mL THF and then discarded. The filtrate was concentrated in vacuo to a liquid which solidified when dried under reduced pressure to yield 30.5 g (100%) of 4-bromophenyl pivalate.

Provenance & Evidence