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

HRID 555410Notes

Reaction equation

HRID 555410 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-75ffc190597c45b0bd966b0bc5309c5f
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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