Hydrochloric Acid → 4-Fluoro-benzenebutanol

Temperature

0 °C

A suspension of aluminium trichloride (10.2 g, 76.5 mmol) in dichloromethane (250 ml) at 0° C. was added with the borane-tert-butylamine complex (13.2 g, 153 mmol) and the mixture was left under stirring at 0° C. for 15 minutes. After that the mixture was added with 3-(4-fluorobenzoyl)propionic acid (5 g, 25.5 mmol) stirring at room temperature for 20 h, then added slowly with 0.2M HCl (75 ml) and extracted with ethyl acetate (3×100 ml). The combined organic phases were washed with 0.2M HCl and with a NaCl saturated solution, dried and the solvents were removed under reduced pressure. The resulting residue was purified by chromatography through a silica gel column, eluting with hexane:ethyl acetate, 8:2, thereby recovering 2.70 g of the title product as a colourless oil (63% yield).

1. additionwas added with the borane-tert-butylamine complex (13.2 g, 153 mmol)
2. waitthe mixture was left
3. stirringstirring at room temperature for 20 h
4. extractionextracted with ethyl acetate (3×100 ml)
5. washThe combined organic phases were washed with 0.2M HCl and with a NaCl saturated solution
6. customdried
7. customthe solvents were removed under reduced pressure
8. customThe resulting residue was purified by chromatography through a silica gel column
9. washeluting with hexane

ORD record

ord-1ea14988f10240a3b00dbf580fc7ad14

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05990142