Iodine → Bis(1,1-dimethylethyl)(1-methyl-2,2-diphenylethenyl)phosphine

Into a reactor were introduced 1.37 g (5.0 mmol) of the 2-bromo-11-diphenylpropene obtained in Example 1 (2), 0.134 g (5.5 mmol) of magnesium, and 11 mL of THF under a nitrogen atmosphere. Iodine and bromobenzene were added to the mixture in a slight amount to ascertain initiation of a reaction. Thereafter, the reaction mixture was refluxed for 2 hours and then cooled. Thereto were added 0.520 g (5.3 mmol) of copper chloride and 1.1 mL (5.5 mmol) of chlorodi-t-butylphosphine. This reaction mixture was refluxed for 18 hours and then cooled to room temperature. Thereto was added 14 mL of heptane. The crystals yielded were taken out by filtration and dissolved in 40 mL of ethyl acetate. The resultant solution was washed with 28% ammonia water and an aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was recrystallized from ethanol to obtain 0.736 g (43%) of the target compound as white crystals.

1. custominitiation of a reaction
2. temperatureThereafter, the reaction mixture was refluxed for 2 hours
3. temperaturecooled
4. temperatureThis reaction mixture was refluxed for 18 hours
5. customThe crystals yielded
6. filtrationwere taken out by filtration
7. dissolutiondissolved in 40 mL of ethyl acetate
8. washThe resultant solution was washed with 28% ammonia water
9. dry with materialan aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate
10. customThereafter, the solvent was removed under reduced pressure
11. customThe concentrate was recrystallized from ethanol

ORD record

ord-a863d69d3db4422399910c6a7a8a89b5

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06455720B1