Triethylamine → (2-Bromopyridin-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

30.2 ml (295 mmol) of triethylamine is added to 56.5 g (280 mmol) of 2-bromo-isonicotinic acid in 1.2 1 of THF. Then, it is cooled to −10° C. and mixed drop by drop with 38.2 ml (295 mmol) of isobutyl chloroformate. After stirring has been continued for one hour at −10° C., it is cooled to −70° C. and mixed drop by drop with 590 ml (590 mmol) of LiAlH4 solution (1 M in THF). After stirring is continued for one hour at −70° C., it is allowed to reach −40° C. 600 ml of 50% acetic acid is added. It is stirred overnight at room temperature. The insoluble components are suctioned off, and the filtrate is concentrated by evaporation. The residue is purified on silica gel with hexane and hexane/ethyl acetate 1:1. 28.0 g of white solidifying oil accumulates.

Provenance & Evidence