Ethanolamine → HCID 2865170, compound

A solution of 1-bromo-2-(2-bromoethoxy)benzene (C21) (5.66 g, 20.22 mmol) and 2-aminoethanol (12.30 g, 202 mmol) in 2-propanol (50 mL) was heated to 80° C. After heating overnight, the reaction mixture was cooled to room temperature and concentrated in vacuo. The resulting residue was taken up in dichloroethane and washed with saturated aqueous sodium bicarbonate solution and water. The organic layer was dried over magnesium sulfate, filtered and the filtrate was concentrated in vacuo to afford the title compound as a clear yellow oil. Yield: 5.12 g, 20.18 mmol, 97%. LCMS m/z 259.9 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.88 (dd, J=5.3, 5.1 Hz, 2H), 3.08 (dd, J=5.1, 5.1 Hz, 2H), 3.67 (dd, J=5.3, 5.3 Hz, 2H), 4.14 (dd, J=5.1, 5.1 Hz, 2H), 6.85 (ddd, J=7.6, 7.6, 1.3 Hz, 1H), 6.91 (dd, J=8.2, 1.2 Hz, 1H), 7.26 (ddd, J=8.2, 7.6, 1.5 Hz, 1H), 7.54 (dd, J=8.0, 1.6 Hz, 1H).

1. temperatureAfter heating overnight
2. concentrationconcentrated in vacuo
3. washwashed with saturated aqueous sodium bicarbonate solution and water
4. dry with materialThe organic layer was dried over magnesium sulfate
5. filtrationfiltered
6. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-791b40dde1c34ca683a06705d9ad5949

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067934B2