2-Tert-Butylphenol → 1-tert-Butyl-2-(2-nitrophenoxy)benzene

HRID 2377808Notes

Reaction equation

HRID 2377808 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 69232-Tert-ButylphenolHCID 69451-Chloro-2-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 154152661-tert-Butyl-2-(2-nitrophenoxy)benzeneYield 122.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-chloronitrobenzene (9.5 g, 60 mmol), 2-t-butyl phenol (9.04 g, 60.2 mmol) and potassium carbonate (10.6 g) in DMF was heated at 130° C. for 6 days. The reaction was cooled to rt and partitioned between diethyl ether (400 mL) and water (500 mL). The organic layer was separated and the aqueous layer was extracted with ether (3×100 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 1-tert-butyl-2-(2-nitrophenoxy)benzene (20 g). (M+H)+=216.23.

Workup

  1. temperatureThe reaction was cooled to rt
  2. custompartitioned between diethyl ether (400 mL) and water (500 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ether (3×100 mL)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-54406fba48aa4b17b8c686b64e9d12a1
Source dataset
uspto-grants-2008_12
Patent number
US07470712B2

Reaction notes

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