4-tert-Butylphenol → HCID 89648362, compound

HRID 929446Notes

Reaction equation

HRID 929446 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[C:12]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([O:22][C:7]2[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=2[F:1])=[CH:20][CH:21]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 89648362HCID 89648362, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following procedure A, 3,4-difluoronitrobenzene (401 mg, 2.52 mmol, 1.00 eq) and 4-tert-butylphenol (477 mg, 3.18 mmol, 1.26 eq) were dissolved in DMSO (6 mL). Anhydrous K2CO3 (522 mg, 3.78 mmol, 1.50 eq) was added and the reaction mixture was stirred at room temperature for 19 h. After extraction with Et2O, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:50) to afford the title compound as colourless oil (722 mg, 2.52 mmol, 99% yield). Rf=0.54 (EtOAc/PE 1:20). HRMS (ESI) calcd. for C16H17FNO3+ [M+H]+ 290.1187. found: 290.1194. 1H NMR (400 MHz, CDCl3) δ 8.07 (dd, J=10.3, 2.7 Hz, 1H, aromatic H), 7.96 (ddd, J=9.1, 2.7, 1.5 Hz, 1H, aromatic H), 7.49-7.38 (m, 2H, aromatic H), 7.09-6.99 (m, 2H, aromatic H), 6.96 (dd, J=9.1, 8.0 Hz, 1H, aromatic H), 1.35 (s, 9H, C(CH3)3). 13C NMR (101 MHz, CDCl3) δ 153.35, 152.23, 151.93, 151.82, 150.84, 148.70, 142.40, 142.33, 127.29, 120.68, 120.64, 119.38, 117.73, 117.71, 113.28, 113.05, 34.65, 31.54.

Workup

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

Sources & evidence

ORD record
ord-f959ec4d078a4a1c8b335e724c710f2a
Source dataset
uspto-grants-2016_03
Patent number
US09296682B2

Reaction notes

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