반응 #216972

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1-bromo-4-iodobenzene

2-bromonaphthalene

t-butyllithium

→

title compound

수율 72.0%

2-(4-Bromophenyl)naphthalene

수율 72.0%

용매

THF

THF

THF

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후처리

1. 1
   온도The resulting light yellow solution was warmed to room temperature
2. 2
   workup.STIRRINGstirred for 1 hour
3. 3
   온도After cooling to -78° C.
4. 4
   workup.WAITAfter an additional 20 min
5. 5
   기타the cooling bath was removed
6. 6
   workup.STIRRINGthe reaction stirred at room temperature for 16 hours
7. 7
   기타quenched with 50 mL of 2M hydrochloric acid
8. 8
   추출The mixture was extracted thrice with ether
9. 9
   세척washed once with saturated sodium bicarbonate solution and once with 10% sodium thiosulfate
10. 10
    추출The organic extract
11. 11
    건조was dried (MgSO4)
12. 12
    기타evaporated
13. 13
    기타The crude product was purified by flash chromatography on silica gel (5×25 cm column, hexanes as elutent)

실험 절차

To a stirred solution of 4.14 g (20.0 mmol) of 2-bromonaphthalene in 50 mL of THF at -78° C. under nitrogen was added a solution of 23.5 mL (40.0 mmol, 1.7M in pentane) of t-butyllithium over 10 minutes. The resulting slurry was stirred for 30 minutes and then warmed to 0° C. for 15 minutes. To this deep indigo solution was added a solution of 3.50 g (25.6 mmol) of thrice-fused zinc chloride in 25 mL of THF. The resulting light yellow solution was warmed to room temperature and stirred for 1 hour. After cooling to -78° C., a solution of 5.66 g (20.0 mmol) 1-bromo-4-iodobenzene and 300 mg (0.26 mmol) of tetrakis(triphenylphosphine)palladium in 20 mL of THF was added over the course of 15 minutes. After an additional 20 min, the cooling bath was removed, the reaction stirred at room temperature for 16 hours and then quenched with 50 mL of 2M hydrochloric acid. The mixture was extracted thrice with ether, the extracts combined, washed once with saturated sodium bicarbonate solution and once with 10% sodium thiosulfate. The organic extract was dried (MgSO4) and evaporated. The crude product was purified by flash chromatography on silica gel (5×25 cm column, hexanes as elutent) to give 4.05 g (72%) of title compound as a white solid, mp 121°-123° C.

출처