Triethylamine → 1,2,3-Trifluorobenzene

Temperature

-78 °C

1.27 g of 3,4,5-trifluorophenol and 870 mg of triethylamine were dissolved in 10 ml of methylene chloride, and the solution was stirred at −78° C. To the solution was added dropwise 5 ml of a methylene chloride solution of 2-(2-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)ethyl)-1,3-dithianilium triflate obtained above (3.8 g), and the to solution was further stirred for one hour. 6.24 ml of Et3N.3HF was then -added, and a methylene chloride solution of bromine (6.24 g) was further added dropwise. After stirring at −70° C. for one hour, the reaction solution was allowed to gradually warm up. It was poured into 100 ml of a cold 3N sodium hydroxide solution at 0° C. and extracted with methylene chloride (30 ml×3). The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting yellow oily substance was isolated and purified by a silica gel column chromatography with heptane as a developing solvent to obtain 1.0 g of 1-(3-(trans-4-propylcyclohexyl)cyclohexyl)-1,1-difluoropropyleneoxy)-3,4,5-trifluorobenzene as colorless crystals. A transition point thereof is shown below.

1. customobtained above (3.8 g)
2. stirringthe to solution was further stirred for one hour
3. stirringAfter stirring at −70° C. for one hour
4. temperatureto gradually warm up
5. extractionextracted with methylene chloride (30 ml×3)
6. washThe organic layer was washed with water
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe resulting yellow oily substance was isolated
10. custompurified by a silica gel column chromatography with heptane as a developing solvent

ORD record

ord-9aef217dbb8a41ecb5109bb04da73b3c

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06544604B2