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

HRID 929443

反応式

HRID 929443 の反応式
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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-b3929b42598e43dda85d67c5e4e565e2
出典データセット
uspto-grants-2016_03
特許番号
US09296682B2

関連ノート

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