1,3,5-Tribromobenzene → HCID 12691335, compound

Temperature

-78 °C

Under a nitrogen atmosphere, 30.0 g (95.0 mmol) of 1,3,5-tribromobenzene and 400 mL of diethyl ether were placed in a 500-mL glass flask and cooled to −78° C. Further, 60 ml (96.0 mmol) of 1.6M n-butyl lithium hexane solution was dropped into the glass flask at −78° C. over 1 hour. The resulting solution was subjected to aging at −78° C. for 1 hour. The lithiation of the raw material was confirmed by gas chromatography. After that, 16.6 g (100.0 mmol) of hexafluoroacetone was charged into the solution at −78° C. and stirred for 1 hour. After the completion of the stirring, the reacted solution was separated into an organic layer and an aqueous layer by the addition of 400 mL of 2N hydrochloric acid. The aqueous layer was extracted with 100 mL of isopropyl ether. The extracted organic layers were combined, dried with anhydrous magnesium sulfate, concentrated by an evaporator, and then, subjected to distillation. With this, 23 g of 1-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-3,5-dibromobenzene was obtained. The yield was 60%.

1. customAfter the completion of the stirring, the reacted solution was separated into an organic layer
2. additionan aqueous layer by the addition of 400 mL of 2N hydrochloric acid
3. extractionThe aqueous layer was extracted with 100 mL of isopropyl ether
4. dry with materialdried with anhydrous magnesium sulfate
5. concentrationconcentrated by an evaporator
6. distillationsubjected to distillation

ORD record

ord-7b3f414b374e4b00a001e6b01623851b

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809451B2