4-Tert-octylphenol → HCID 89648304, compound

HRID 929451Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:25][C:22]2[CH:23]=[CH:24][C:19]([C:11]([CH3:13])([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:12])=[CH:20][CH:21]=2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 40 °C

Procedure

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.

Workup

extractionAfter extraction with Et2O
customthe crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:50)

Sources & evidence

ORD record: ord-af656342dcd34b0b86159e8278e4f431
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296682B2

Reaction notes

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