Dimethyl Sulfoxide → 1-(2-Methylbutan-2-yl)-4-(4-nitrophenoxy)benzene

HRID 929443

Reaktionsgleichung

Reaktionsgleichung von HRID 929443
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)([CH2:14][CH3:15])([CH3:13])[CH3:12].CS(C)=O>>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:22][C:19]2[CH:20]=[CH:21][C:16]([C:11]([CH2:14][CH3:15])([CH3:12])[CH3:13])=[CH:17][CH:18]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Komponenten

4

Edukt 3

HCID 679Dimethyl SulfoxideHCID 66434-tert-PentylphenolHCID 9590p-Fluoronitrobenzene

Produkt 1

HCID 37191911-(2-Methylbutan-2-yl)-4-(4-nitrophenoxy)benzeneAusbeute 83,1 %

Versuchsvorschrift

Following procedure A, 4-fluoronitrobenzene (318 mg, 2.25 mmol, 1.00 eq) and 4-tert-pentylphenol (460 mg, 2.28 mmol, 1.24 eq) were dissolved in DMSO (6 mL) Anhydrous K2CO3 (465 mg, 3.37 mmol, 1.49 eq) was added and the reaction mixture was stirred at room temperature for 2 h. After extraction with Et2O, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100) to afford the title compound as colourless solid (533 mg, 1.87 mmol, 83% yield). Rf=0.70 (EtOAc/PE 1:20). HRMS (ESI) calcd. for C17H20NO3+ [M+H]+ 285.1365. found: 285.1359. 1H NMR (400 MHz, CDCl3) δ 8.25-8.14 (m, 2H, aromatic H), 7.44-7.32 (m, 2H, aromatic H), 7.06-6.96 (m, 4H, aromatic H), 1.66 (q, J=7.4 Hz, 2H, Ar—C(CH3)2CH2CH3), 1.31 (s, 6H, Ar—C(CH3)2CH2CH3), 0.71 (t, J=7.4 Hz, 3H, Ar—C(CH3)2CH2CH3). 13C NMR (101 MHz, CDCl3) δ 163.81, 152.24, 146.94, 142.56, 127.91, 126.01, 120.06, 116.99, 37.89, 37.06, 28.63, 9.27.

Aufarbeitung

  1. additionwas added
  2. extractionAfter extraction with Et2O
  3. customthe crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100)

Quellen und Nachweise

ORD-Eintrag
ord-b3929b42598e43dda85d67c5e4e565e2
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296682B2

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