Hydrochloric Acid → Benzaldehyde, 3-(4-fluorophenoxy)-

Temperature

-75 °C

To a cooled (-75° C.), stirred solution of 1-bromo-3-(4-fluorophenoxy)benzene (38.5 g; 0.1442M) in dry THF (80 ml) was added n-butyllithium (1.63M in n-hexane, 68 ml; 0.11M) dropwise at under N2. After stirring for 30 min at -73° C., DMF (11.38 g; 0.1557M) was added dropwise to the mixture at -73° C. The mixture was stirred for further 30 min, and then allowed to warm to room temperature. 2M aqueous HCl (200 ml) was added to the mixture and the whole was extracted with Et2O (100 ml×3). The combined organic layers were washed with water (150 ml), brine (150 ml), dried over MgSO4, and concentrated in vacuo. The residual oil was purified by flash column (SiO2) eluting with ethyl acetate-n-hexane (1: 10) to give 21.6 g of the subtitle compound [B] as a colorless oil.

1. stirringThe mixture was stirred for further 30 min
2. temperatureto warm to room temperature
3. extractionthe whole was extracted with Et2O (100 ml×3)
4. washThe combined organic layers were washed with water (150 ml), brine (150 ml)
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. customThe residual oil was purified by flash column (SiO2)
8. washeluting with ethyl acetate-n-hexane (1: 10)

ORD record

ord-73a9e15b9ab3426c90984a1c3d9cf008

Source dataset

uspto-grants-1998_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05792882