Réaction #57067

Équation de réaction

MeOH

tetrabromo para-xylene

furan

BuLi

→

26

Rendement 50.0%

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

Rendement 50.0%

Solvants

PhMe

water

Conditions de réaction

Traitement

1. 1
   Températureto warm to rt
2. 2
   workup.WAITAfter 3 hours
3. 3
   AutreThe organic layer was separated
4. 4
   Extractionthe aqueous layer was extracted three times with Et2O
5. 5
   LavageThe combined organic layers were washed with brine
6. 6
   Séchagedried over MgSO4
7. 7
   Concentrationconcentrated

Mode opératoire

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

Source