Azobisisobutyronitrile → HCID 68506530, compound

Temperature

80 °C

A mixture of 4-bromo-2-fluoro-5-methylbenzonitrile, AIBN (0.1 eq.) and NBS (1 eq.) in CCl4 (0.14 M) was stirred at 80° C. for 18 h. After cooling to RT the mixture was quenched with 1N aq. NaS2O3 and extracted with DCM. The organic phase was washed with brine, dried (Na2SO4), and concentrated to dryness under reduced pressure. The residue was dissolved in MeCN (0.2 M), then trimethylsilyl cyanide (1 eq.) was added, followed by TBAF (1M in THF, 1 eq.). The mixture was stirred for 2 h at RT, and then water was added and the solvents were removed under reduced pressure. The residue was diluted with DCM, washed with brine, dried (Na2SO4), and concentrated to dryness under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with 5-50% EtOAc/petroleum ether to afford the product as a white solid. 1H-NMR (300 MHz, CDCl3) δ: 7.78 (1H, d, J=6.3 Hz), 7.55 (1H, d, J=7.8 Hz), 3.82 (2H, s). MS (ES) C9H4BrFN2 requires: 238/240, found: 237/239 (M−H)−.

1. temperatureAfter cooling to RT the mixture
2. customwas quenched with 1N aq. NaS2O3
3. extractionextracted with DCM
4. washThe organic phase was washed with brine
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated to dryness under reduced pressure
7. dissolutionThe residue was dissolved in MeCN (0.2 M)
8. stirringThe mixture was stirred for 2 h at RT
9. customthe solvents were removed under reduced pressure
10. additionThe residue was diluted with DCM
11. washwashed with brine
12. dry with materialdried (Na2SO4)
13. concentrationconcentrated to dryness under reduced pressure
14. customThe crude product was purified by column chromatography on silica gel eluting with 5-50% EtOAc/petroleum ether

ORD record

ord-e6f2dcd266d443508b3cfe22ba41caee

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268827B2