Trimethyl borate → HCID 87293355, compound

In a solution of 2.58 g of 3-chloro-2-fluoro-5-iodobenzotrifluoride and 0.68 g of tert-butylmethyl ether in 20 mL of hexane, 6.0 mL of n-butyl lithium (1.54M hexane solution) was added dropwise at −20° C. with stirring, and stirred at the same temperature for 30 minutes. Then, a solution of 0.88 g of trimethoxyborane in 10 mL of tetrahydrofuran was added dropwise. After the completion of the addition dropwise, it was stirred at the same temperature further for 30 minutes and then the temperature was raised to room temperature. Then, in the reaction mixture, 4.00 g of 2-bromo-3,3,3-trifluoropropene, 2.20 g of potassium carbonate, 15 mL of water and 0.03 g of 1,3-bis(2,6-diisopropylphenyl)imidazole-2-ilidene (1,4-naphthoquinone) palladium (0) dimmer were added, and stirred under nitrogen atmosphere at 60° C. for 6 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, insoluble material was filtered off, and the organic phase was collected and the aqueous phase was extracted with 30 mL of diethyl ether twice. The combined organic phases were washed with water, and dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with hexane to obtain 1.70 g of the aimed product as yellow oily substance.

1. stirringstirred at the same temperature for 30 minutes
2. additionAfter the completion of the addition dropwise
3. stirringit was stirred at the same temperature further for 30 minutes
4. stirringstirred under nitrogen atmosphere at 60° C. for 6 hours
5. customAfter the completion of the reaction
6. waitthe reaction mixture was left
7. temperaturecooled to room temperature
8. filtrationinsoluble material was filtered off
9. customthe organic phase was collected
10. extractionthe aqueous phase was extracted with 30 mL of diethyl ether twice
11. washThe combined organic phases were washed with water
12. dry with materialdried over saturated sodium chloride aqueous solution
13. distillationanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure
14. customThe residue was purified with silica gel column chromatography that

ORD record

ord-903b428003534a1a9f6cd6a494a5d2ef

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07951828B1