4-tert-Butylphenol → HCID 3783522, compound

HRID 929441Notes

Reaction equation

HRID 929441 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:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:11]([C:15]1[CH:16]=[CH:17][C:18]([O:21][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:19][CH:20]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 3783522HCID 3783522, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following procedure A, 4-fluoronitrobenzene (500 mg, 3.54 mmol, 1.00 eq) and 4-tert-butylphenol (671 mg, 4.46 mmol, 1.26 eq) were dissolved in DMF (6.0 mL). Anhydrous K2CO3 (857 mg, 6.20 mmol, 1.75 eq) was added and the reaction mixture was stirred at room temperature for 52 h. After extraction with EtOAc, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100) to afford the title compound as pale yellow solid (860 mg, 3.17 mmol, 89% yield). Rf=0.72 (EtOAc/PE 1:9). HRMS (ESI) calcd. for C16H18NO3+ [M+H]+ 272.1281. found: 272.1272. 1H NMR (400 MHz, CDCl3) δ 8.24-8.16 (m, 2H, aromatic H), 7.49-7.39 (m, 2H, aromatic H), 7.06-6.97 (m, 4H, aromatic H), 1.35 (s, 9H, C(CH3)3). 13C NMR (101 MHz, CDCl3) δ 163.82, 152.29, 148.59, 142.54, 127.27, 126.03, 120.15, 116.98, 34.67, 31.58.

Workup

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

Sources & evidence

ORD record
ord-d85dec6c7a5f41889b216b47d173cfc9
Source dataset
uspto-grants-2016_03
Patent number
US09296682B2

Reaction notes

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