2-Bromoethanol → HCID 85858301, compound

To a solution of 4-diethylamino-2-hydroxybenzaldehyde (1.00 g, 5.17 mmol) in 10 mL of dry N,N-dimethylformamide was added sodium hydride (250 mg, 55%, 5.7 mmol) under nitrogen at 0° C. After the reaction mixture was stirred at room temperature for 30 min, 2-bromoethanol (1.1 mL, 15 mmol) was added with additional stirring at 50° C. overnight. After quench with NH4Cl aqueous solution at 0° C., the solution was extracted with ethyl acetate three times. The extracts were washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 25/75) to obtain the title compound as a brown gum (566 mg, 46%).

1. stirringwith additional stirring at 50° C. overnight
2. customAfter quench with NH4Cl aqueous solution at 0° C.
3. extractionthe solution was extracted with ethyl acetate three times
4. washThe extracts were washed with saturated NaHCO3 aqueous solution, brine
5. dry with materialdried over MgSO4
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated in vacuo
8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 25/75)

ORD record

ord-02896a1b0a3c4392be1c563b661e4b5a

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962674B2