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

HRID 929443

Reaction equation

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]

Participants

Reactant 3

HCID 679Dimethyl Sulfoxide

HCID 66434-tert-Pentylphenol

HCID 9590p-Fluoronitrobenzene

Product 1

HCID 37191911-(2-Methylbutan-2-yl)-4-(4-nitrophenoxy)benzeneYield 83.1%

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-b3929b42598e43dda85d67c5e4e565e2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296682B2

Linked notes

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