p-Fluoronitrobenzene → Benzene, 1-cyclohexyl-4-(4-nitrophenoxy)-

HRID 929444Notes

Reaction equation

HRID 929444 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH:11]1([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH:11]1([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:2]3[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=3)=[CH:21][CH:22]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 143274-Cyclohexylphenol

Product 1

HCID 106353Benzene, 1-cyclohexyl-4-(4-nitrophenoxy)-Yield 93.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following procedure A, 4-fluoronitrobenzene (325 mg, 2.30 mmol, 1.00 eq) and 4-cyclohexylphenol (519 mg, 2.94 mmol, 1.28 eq) were dissolved in DMSO (6 mL). Anhydrous K2CO3 (513 mg, 3.72 mmol, 1.61 eq) was added and the reaction mixture was stirred at room temperature for 48 h. After extraction with Et2O, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100 to 1:50) to afford the title compound as pale yellow solid (640 mg, 2.15 mmol, 93% yield). Rf=0.55 (EtOAc/PE 1:20). HRMS (ESI) calcd. for C18H20NO3+ [M+H]+ 298.1438. found: 298.1442. 1H NMR (400 MHz, CDCl3) δ 8.31-8.11 (m, 2H, aromatic H), 7.26 (d, J=2.3 Hz, 2H, aromatic H), 7.13-6.92 (m, 4H, aromatic H), 2.57-2.50 (m, 1H, cyclohexyl H), 2.09-1.67 (m, 5H, cyclohexyl H), 1.59-1.18 (m, 5H, cyclohexyl H). 13C NMR (101 MHz, CDCl3) δ 163.89, 152.61, 145.58, 142.57, 128.66, 126.04, 120.49, 116.99, 44.14, 34.72, 26.99, 26.23.

Workup

  1. extractionAfter extraction with Et2O
  2. customthe crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100 to 1:50)

Sources & evidence

ORD record
ord-ab715fb36f1546c2a54f51257b09f832
Source dataset
uspto-grants-2016_03
Patent number
US09296682B2

Reaction notes

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