Reacción #533580

Ecuación de reacción

potassium carbonate

1-bromo-3-(2-methoxyvinyl)-2-methylbenzene

→

subtitled compound

2-(3-Bromo-2-methylphenyl)ethanol

Disolventes

water

—

ice water

THF

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthe solution was filtered
2. 2
   workup.DISSOLUTIONdissolved/part
3. 3
   workup.ADDITIONadded to the reaction mixture from above
4. 4
   OtroA grey, cloudy, two-phase mixture was formed
5. 5
   Extracciónextracted twice with ethyl acetate
6. 6
   LavadoThe combined organic phases were washed with brine
7. 7
   Secadodried (MgSO4)
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated in vacuo

Procedimiento

To an ice-cold solution of 1-bromo-3-(2-methoxyvinyl)-2-methylbenzene [Aromatic Intermediate 22, step a] (1.75 g) in THF (25 mL) was added a solution of mercury(II) acetate (2.95 g) in water (30 mL) and the resulting solution was stirred in ice-water for 2.75 hours. Meanwhile, potassium carbonate (35 g) was dissolved in water (30 mL) and the solution was filtered. Sodium borohydride (1.17 g) was part dissolved/part suspended in 35 mL of the resulting potassium carbonate solution, and added to the reaction mixture from above. A grey, cloudy, two-phase mixture was formed, that was stirred at room temperature for 2.5 hours, then poured into water and extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to afford the subtitled compound as a colourless oil. Yield 1.67 g.

Fuente