Reaktion #57067

Reaktionsgleichung

MeOH

tetrabromo para-xylene

furan

BuLi

→

26

Ausbeute 50.0%

5,6-Dibromo-4,7-dimethyl-1,4-epoxy-1,4-dihydronapthalene

Ausbeute 50.0%

Lösungsmittel

PhMe

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to rt
2. 2
   workup.WAITAfter 3 hours
3. 3
   SonstigeThe organic layer was separated
4. 4
   Extraktionthe aqueous layer was extracted three times with Et2O
5. 5
   WaschenThe combined organic layers were washed with brine
6. 6
   Trocknendried over MgSO4
7. 7
   Einengenconcentrated

Vorschrift

To tetrabromo para-xylene (2.1 g, 5.0 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silca gel gave 26 (185 mg, 50%) as a white solid. The spectral data correlates well with the literature values. 22

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