Hydrochloric Acid → 2-Bromo-1-[4-(8-hydroxyoctyl)phenyl]ethanone

Temperature

0 °C

Aluminium chloride (200 mg, 1.50 mmol, 3.0 eq.) was suspended in dry dichloromethane (8 mL) and cooled to 0° C. 8-phenyl-1-octanol (0.11 mL, 0.50 mmol) and bromo acetylbromide (53 μL, 0.60 mmol, 1.2 eq.) were added dropwise. After 20 min the mixture was warmed to r.t. and stirred overnight. The reaction was stopped by pouring the solution into a mixture of ice water (25 mL) and concentrated hydrochloric acid (10 mL). The phases were separated and the aqueous layer was extracted with dichloromethane (2×10 mL). The combined organic phases were washed with saturated sodium bicarbonate solution (1×10 mL) and brine (1×10 mL) and dried over MgSO4. The solvent was evaporated and the residue was purified by column chromatography (silica gel, 12×4 cm, cyclohexane/ethyl acetate, 8:1). The product was isolated as colourless oil. Yield: 120 mg (73%).

1. temperatureAfter 20 min the mixture was warmed to r.t.
2. additionby pouring the solution
3. customThe phases were separated
4. extractionthe aqueous layer was extracted with dichloromethane (2×10 mL)
5. washThe combined organic phases were washed with saturated sodium bicarbonate solution (1×10 mL) and brine (1×10 mL)
6. dry with materialdried over MgSO4
7. customThe solvent was evaporated
8. customthe residue was purified by column chromatography (silica gel, 12×4 cm, cyclohexane/ethyl acetate, 8:1)
9. customThe product was isolated as colourless oil

ORD record

ord-76c3a708f5fc48b08a4243257d64e522

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09345791B2