Dimethylformamide → 2-Chloro-1-(2-methoxyethoxy)-4-nitrobenzene

Temperature

50 °C

2-Chloro-1-fluoro-4-nitrobenzene (0.8 g, 4.56 mmol) and 2-(methyloxy)ethanol (0.52 g, 6.84 mmol) were combined and dissolved in Acetonitrile (15 mL). Potassium carbonate (2.4 g, 17 mmol) was then added and the resulting mixture was heated at 50° C. for 16 h. The reaction was not complete so additional potassium carbonate (1.0 g, 7.24 mmol) and 2-(methyloxy)ethanol (0.08 g, 1.05 mmol) were added as well as DMF (3 mL) to aid in solubilizing the reaction which was then heated at 85° C. for 16 h. The reaction was cooled to rt then diluted with EtOAc (250 mL) and water (150 mL). The organic layer was separated, washed with brine (100 mL), dried over Na2SO4, filtered and concentrated in vacuo to yield 1.0 g of the compound. 1H NMR (300 MHz, DMSO-d6): δ 8.31 (d, 1H), 8.21 (m, 1H), 7.38 (d, 1H), 4.35 (m, 2H), 3.72 (m, 2H), 3.32 (s, 3H).

1. customthe reaction which
2. temperaturewas then heated at 85° C. for 16 h
3. temperatureThe reaction was cooled to rt
4. customThe organic layer was separated
5. washwashed with brine (100 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-65d289923f344eb5b2a509ee71d7beae

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07812022B2