4-Tert-octylphenol → HCID 89648304, compound

Participants

Reaction Conditions

Reaction Steps

Following procedure A, 2-Chloro-5-nitropyridine (303 mg, 1.91 mmol, 1.00 eq) and 4-tert-octylphenol (495 mg, 2.40 mmol, 1.25 eq) were dissolved in DMSO (5 mL). Anhydrous K2CO3 (426 mg, 3.08 mmol, 1.61 eq) was added and the reaction mixture was stirred at 40° C. for 28 h. After extraction with Et2O, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:50) to afford the title compound as colourless solid (598 mg, 1.82 mmol, 95% yield). Rf=0.65 (EtOAc/PE 1:10). HRMS (ESI) calcd. for C19H25N2O3+ [M+H]+ 329.1860. found: 329.1854. 1H NMR (400 MHz, CDCl3) δ 9.07 (d, J=2.8 Hz, 1H, aromatic H), 8.45 (dd, J=9.1, 2.8 Hz, 1H, aromatic H), 7.52-7.40 (m, 2H, aromatic H), 7.14-7.03 (m, 2H, aromatic H), 6.97 (d, J=9.1 Hz, 1H, aromatic H), 1.76 (s, 2H, Ar—C(CH3)2CH2C(CH3)3), 1.40 (s, 6H, Ar—C(CH3)2CH2C(CH3)3), 0.75 (s, 9H, Ar—C(CH3)2CH2C(CH3)3). 13C NMR (101 MHz, CDCl3) δ 167.24, 150.49, 148.12, 145.30, 140.29, 134.92, 127.78, 120.57, 111.15, 57.28, 38.63, 32.55, 31.93, 31.62.

Provenance & Evidence