Potassium Carbonate → 2-(3-Bromo-2-methylphenyl)ethan-1-ol

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.

1. filtrationthe solution was filtered
2. dissolutiondissolved/part
3. additionadded to the reaction mixture from above
4. customA grey, cloudy, two-phase mixture was formed
5. extractionextracted twice with ethyl acetate
6. washThe combined organic phases were washed with brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-0e99c0e2e8f548b1a6fb9f6ef9c16959

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476265B2