Sulfuric Acid → 6-Bromo-5,5,6,6-tetrafluorohexan-1-ol

Participants

Reaction Conditions

Reaction Steps

In nitrogen atmosphere, 500 g (1.75 mol) of 6-bromo-5,5,6,6-tetrafluorohexanoyl chloride was dissolved in 1500 mL of ethylene glycol dimethyl ether, followed by the addition of 53 g (1.40 mol) of sodium borohydride. Upon stirring it at 50° C. for 2 hours, a reaction solution was added to a diluted sulfuric acid aqueous solution, followed by extraction with diisopropyl ether. (At this time, the reaction solution was analyzed by gas chromatography, thereby confirming that the production ratio of the objective product 6-bromo-5,5,6,6-tetrafluorohexan-1-ol to the by-product 5,5,6,6-tetrafluorohexan-1-ol was 100%:0%. See Table 1.) After distilling a solvent off, distillation under reduced pressure (113° C./3.8 kPa) was conducted, thereby obtaining 332 g of the objective 6-bromo-5,5,6,6-tetrafluorohexan-1-ol in the form of a colorless transparent liquid (94% yield, 99.3% GC purity).

Provenance & Evidence