Dimethylformamide → 2,2'-Difluoro-6-nitro-1,1'-biphenyl

Temperature

110 °C

To a solution of 2-bromo-3-fluoronitrobenzene (1.500 g, 6.8 mmol), 2-fluorophenylboronic acid (1.145 g, 8.2 mmol), N,N-dimethylformamide (50 mL), and 2.0 M aqueous potassium carbonate (10 mL) under argon was added tetrakis(triphenylphosphine)palladium (0) (0.394 g, 0.3 mmol). The mixture was stirred at 110° C. for 16 hrs. After cooling to room temperature, the mixture was diluted with ethyl acetate (100 mL) and washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-30% methylene chloride/hexanes) to afford a pale yellow solid (0.780 g, 49%). 1H NMR (300 MHz, CDCl3) δ 7.86 (dt, 1H, J=7.8, 1.2 Hz), 7.56 (td, 1H, J=8.1, 5.7 Hz), 7.52-7.40 (m, 2H), 7.35-7.15 (m, 3H).

1. temperatureAfter cooling to room temperature
2. washwashed with saturated aqueous sodium chloride
3. dry with materialdried (anhydrous sodium sulfate)
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was purified by silica gel chromatography (0-30% methylene chloride/hexanes)

ORD record

ord-63cad70ac3414d00a307f07594e61a98

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09265772B2