Sodium Carbonate → 3-(4-bromophenyl)benzonitrile

Temperature

75 °C

To a magnetically stirring solution of 3-cyanophenyl boronic acid (0.62 g, 4.24 mmol) and 1-bromo-4-iodobenzene (1.0 g, 3.53 mmol) in anhydrous DMF (7.0 mL), under argon at room temperature, was added 2M sodium carbonate solution (7.0 mL) followed by Pd(PPh3)4 (0.21 g, 0.18 mmol). The resulting mixture was heated to 75° C. overnight. The resulting dark reaction mixture was cooled to room temperature filtered to remove the solids and the resultant filtrate was poured into water (50 mL) and extracted with EtOAc (2×25 mL). The organics were washed with water (50 mL) and brine (50 mL) then dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (5% EtOAc in Hexanes) to yield the intermediate bromide as a white solid (0.36 g, 33%). 1H NMR (CDCl3): δ 1H NMR (CDCl3) δ: 7.43 (d, J=7.4 Hz, 2H), 7.53-7.67 (m, 4H), 7.76-7.84 (m, 2H).

1. customThe resulting dark reaction mixture
2. temperaturewas cooled to room temperature
3. filtrationfiltered
4. customto remove the solids
5. additionthe resultant filtrate was poured into water (50 mL)
6. extractionextracted with EtOAc (2×25 mL)
7. washThe organics were washed with water (50 mL) and brine (50 mL)
8. dry with materialthen dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude residue was purified by flash chromatography (5% EtOAc in Hexanes)

ORD record

ord-8cbb73193d5049f8ac24f53a07f998f4

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473790B2