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-084620c4ea8949f6b758f75178498daa

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08581009B2