Dimethylformamide → HCID 57470259, compound

Temperature

205 °C

To a solution of 2-bromo-1-tert-butyl-4-nitrobenzene (2.13 g, 8.2 mmol) and Zn(CN)2 (770 mg, 6.56 mmol) in DMF (10 mL) was added Pd(PPh3)4 (474 mg, 0.41 mmol) under a nitrogen atmosphere. The mixture was heated in a sealed vessel at 205° C. for 5 h. After cooling to room temperature, the mixture was diluted with water and extracted with EtOAc twice. The combined organic layers were washed with brine and dried over MgSO4. After removal of solvent, the residue was purified by column chromatography (0-10% EtOAc-Hexane) to give 2-tert-butyl-5-nitrobenzonitrile (1.33 g, 80%). 1H NMR (400 MHz, CDCl3) δ 8.55 (d, J=2.3 Hz, 1H), 8.36 (dd, J=8.8, 2.2 Hz, 1H), 7.73 (d, J=8.9 Hz, 1H), 1.60 (s, 9H); HPLC ret. time 3.42 min, 10-100% CH3CN, 5 min gradient.

1. temperatureAfter cooling to room temperature
2. extractionextracted with EtOAc twice
3. washThe combined organic layers were washed with brine
4. dry with materialdried over MgSO4
5. customAfter removal of solvent
6. customthe residue was purified by column chromatography (0-10% EtOAc-Hexane)

ORD record

ord-2e3b1e2b6acc4c3887bd7c23491a24fa

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829204B2