反应详情

An oven-dried flask under argon was charged with 4-bromo-3,5-dimethoxybenzaldehyde (5.0 g, 20.4 mmol) and anhydrous THF (30 mL). The mixture was cooled over ice then a solution of ethyl magnesium bromide (3.0 M in diethyl ether, 8.2 mL, 24.5 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 hrs. 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 CH2Cl2 and concentrated in vacuo again to give 1-(4-bromo-3,5-dimethoxyphenyl)propan-1-ol as a clear oil (5.43 g, 97% yield). The product was used without further purification.

1. temperatureThe mixture was cooled over ice
2. stirringstirred for 19 hrs
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 CH2Cl2
12. concentrationconcentrated in vacuo again