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

HRID 929443

반응식

HRID 929443 반응식
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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-b3929b42598e43dda85d67c5e4e565e2
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296682B2

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