Water → HCID 86242284, compound

Temperature

80 °C

To a mixture of 1-chloro-2-nitrobenzene (0.5 g, 3.2 mmol) and sodium carbonate (0.34 g, 3.2 mmol) in a 100 mL roundbottom flask equipped with a magnetic stir bar and nitrogen inlet were added water (3.2 mL), dioxane (13 mL) and 2-(cyclopent-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.77 mL, 3.8 mmol). The reaction flask was evacuated and purged with nitrogen (2×) prior to the addition of bis(triphenylphosphine)palladium(II) chloride (0.18 g, 0.25 mmol), and then evacuated and purged (3×) following the addition of the catalyst. The reaction was heated to 80° C. and stirred overnight. The reaction was cooled and filtered through a pad of Celite® which was subsequently washed with water and ethyl acetate. The phases were separated and the organic phase was dried by passing it through a phase separator cartridge and concentrated. The residue was purified by flash column chromatography providing the title compound (0.56 g, 3.0 mmol, 93% yield) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 7.78-7.71 (m, 1H), 7.54-7.47 (m, 1H), 7.40-7.32 (m, 2H), 5.86-5.82 (m, 1H), 2.63-2.55 (m, 2H), 2.55-2.47 (m, 2H), 2.09-1.98 (m, 2H); 13C NMR (101 MHz, CDCl3) δ 148.77, 139.96, 133.58, 132.08, 130.87, 130.52, 127.55, 123.70, 35.31, 33.49, 24.05; ESIMS m/z 190 ([M+H]+).

1. customequipped with a magnetic stir bar and nitrogen inlet
2. customThe reaction flask was evacuated
3. custompurged with nitrogen (2×)
4. customevacuated
5. custompurged (3×)
6. additionthe addition of the catalyst
7. temperatureThe reaction was cooled
8. filtrationfiltered through a pad of Celite® which
9. washwas subsequently washed with water and ethyl acetate
10. customThe phases were separated
11. customthe organic phase was dried
12. concentrationconcentrated
13. customThe residue was purified by flash column chromatography

ORD record

ord-41c2216237da4b8e8a9a725f93d41e91

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916183B2