Ethanol → 4-Bromo-2-ethoxy-1-nitrobenzene

Temperature

0 °C

To a cooled (0° C.) solution of EtOH (0.07 mL, 1.193 mmol) in THF (5 mL) was added NaH (60% suspension in mineral oil, 68 mg, 1.705 mmol). The reaction mixture was stirred under nitrogen at 0° C. for 15 minutes. 2-fluoro-4-bromo-nitrobenzene (250 mg, 1.136 mmol) was added and the reaction mixture stirred for a further 18 hours, whilst warming slowly to room temperature. The reaction mixture was concentrated in vacuo. Ether (20 mL) and HCl (0.5 M, 20 mL) were added. The aqueous layer was basified with aqueous saturated NaHCO3 solution and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo, to give the title compound (270 mg, 97%).

1. stirringthe reaction mixture stirred for a further 18 hours
2. temperaturewhilst warming slowly to room temperature
3. concentrationThe reaction mixture was concentrated in vacuo
4. additionEther (20 mL) and HCl (0.5 M, 20 mL) were added
5. extractionextracted with EtOAc (3×20 mL)
6. washThe combined organic layers were washed with brine (20 mL)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo

ORD record

ord-dfa140a1f12943f79d84045b6916d9fc

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409907B2