Hydrochloric Acid → 2-Bromo-2,2-difluoroethyl pivalate

A glass flask equipped with a thermometer, a condenser and a dropping funnel was charged with 271 g (2.24 moles) of pivaloyl chloride, 360 g (2.23 moles) of 2-bromo-2,2-difluoroethanol and 1.5 L of diisopropyl ether, followed by stirring. Then, 318 g (3.14 moles) of triethylamine was added dropwise thereto, in an iced bath. After the termination of the dropping, stirring was conducted for 1 hour at room temperature. Then, the termination of the reaction was confirmed by gas chromatography. With the addition of 300 mL of water, a reaction solution was completely dissolved therein, followed by adding 500 mL of 2N hydrochloric acid thereto. The reaction solution was separated into an organic layer and a water layer, followed by extracting the water layer with 500 ml of diisopropyl ether. Subsequently, the organic layer was rinsed with 500 ml of saturated brine, followed by drying with anhydrous sodium sulfate. Thereafter, a solvent was distilled off, thereby obtaining 485 g (82% yield, 93% purity) of 2-bromo-2,2-difluoroethyl pivalate in the form of a light yellow liquid.

1. customA glass flask equipped with a thermometer, a condenser and a dropping funnel
2. stirringAfter the termination of the dropping, stirring
3. dissolutiona reaction solution was completely dissolved
4. customThe reaction solution was separated into an organic layer
5. extractionby extracting the water layer with 500 ml of diisopropyl ether
6. washSubsequently, the organic layer was rinsed with 500 ml of saturated brine
7. dry with materialby drying with anhydrous sodium sulfate
8. distillationThereafter, a solvent was distilled off

ORD record

ord-88f352f510b0436e8ed7d3da8ab8e6bb

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748672B2