반응 #439461

반응 방정식

3,4,5-trifluorobromobenzene

magnesium

trimethoxy borane

hydrochloric acid

potassium phosphate

2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl trifluoromethanesulfonate

3,4,5-trifluorophenylboric acid

→

2-propyl-6-(3,4,5-trifluorophenyl)-1,2,3,4-tetrahydronaphthalene

수율 13.9%

용매

water

dimethyl formamide

반응 조건

후처리

1. 1
   기타was produced
2. 2
   온도The mixture was subsequently cooled to room temperature
3. 3
   추출the mixture was extracted with toluene
4. 4
   세척the organic layer was washed subsequently with water
5. 5
   건조a saturated aqueous solution of sodium chloride, and subsequently dried over anhydrous sodium sulfate
6. 6
   기타The crude product obtained by removal of the solvent by evaporation
7. 7
   기타was purified by silica gel column chromatography (hexane)
8. 8
   기타recrystallized 3 times from ethanol

실험 절차

A mixture of 3.8 g of the produced 2-propyl-1,2,3,4-tetrahydronaphthalen-6-yl trifluoromethanesulfonate, 3.0 g of 3,4,5-trifluorophenylboric acid (this compound was produced by reacting a Grignard reagent prepared from 3,4,5-trifluorobromobenzene and magnesium, with trimethoxy borane, and then performing a hydrolysis with dilute hydrochloric acid), 0.13 g of tetrakis(triphenylphosphine)palladium(0), and 3.6 g of potassium phosphate in 20 ml of dimethyl formamide (DMF) was stirred for 10 hours at 80° C. The mixture was subsequently cooled to room temperature, 20 ml of water was added, the mixture was extracted with toluene, and the organic layer was washed subsequently with water and then a saturated aqueous solution of sodium chloride, and subsequently dried over anhydrous sodium sulfate. The crude product obtained by removal of the solvent by evaporation was purified by silica gel column chromatography (hexane) and then recrystallized 3 times from ethanol to obtain 0.5 g of 2-propyl-6-(3,4,5-trifluorophenyl)-1,2,3,4-tetrahydronaphthalene.

출처