4-Bromo-3,5-dimethoxybenzaldehyde → 1-(4-Bromo-3,5-dimethoxyphenyl)ethanol

Temperature

-78 °C

An oven-dried flask under argon was charged with 4-bromo-3,5-dimethoxybenzaldehyde (10.08 g, 41.1 mmol) and anhydrous THF (70 mL). The mixture was cooled over a −78° C. bath then a solution of MeMgBr (3.0 M in diethyl ether, 17.8 mL, 53.4 mmol) was added dropwise from an addition funnel over a period of 45 min. After stirring for 20 min, the mixture was allowed to warm to room temperature and stirred for 19 hours. After quenching with a solution of aqueous NH4Cl, it was diluted with H2O and EtOAc then cooled over an ice bath. After the mixture was cooled, the layers were separated. The organics were washed with H2O and brine then dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in dichloromethane and concentrated in vacuo again to give 1-(4-bromo-3,5-dimethoxyphenyl)ethanol as a white solid (10.8 g, quantitiative yield). The product was used without further purification.

1. temperatureto warm to room temperature
2. stirringstirred for 19 hours
3. customAfter quenching with a solution of aqueous NH4Cl, it
4. additionwas diluted with H2O and EtOAc
5. temperaturethen cooled over an ice bath
6. temperatureAfter the mixture was cooled
7. customthe layers were separated
8. washThe organics were washed with H2O and brine
9. dry with materialthen dried over Na2SO4
10. concentrationconcentrated in vacuo
11. dissolutionThe residue was dissolved in dichloromethane
12. concentrationconcentrated in vacuo again
13. customto give

ORD record

ord-7ffc740fde8b49278d34bd4af662ed1c

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102643B2