Triethylamine → 4-Methyl-1-nitro-3-[4-(trifluoromethoxy)phenoxy]benzene

HRID 1363662Notes

Reaction equation

HRID 1363662 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[F:12][C:13]([F:25])([F:24])[O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][C:18]1[CH:17]=[CH:16][C:15]([O:14][C:13]([F:12])([F:24])[F:25])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 935762-Methyl-5-nitrophenolHCID 27343864-(Trifluoromethoxy)phenylboronic acid

Product 1

HCID 598209394-Methyl-1-nitro-3-[4-(trifluoromethoxy)phenoxy]benzeneYield 20.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-methyl-5-nitrophenol (765 mg, 5.00 mmol), 4-(trifluoromethoxy)benzeneboronic acid (1.24 g, 6.00 mmol), copper(II) acetate (999 mg, 5.50 mmol), triethylamine (3.48 ml, 25.0 mmol), molecular sieves 4A and dichloromethane (20.0 ml) was stirred at room temperature overnight under argon atmosphere. The reaction mixture was filtered through celite. The residue obtained by evaporation of the solvent of the filtrate under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=20:1) to give the title compound (323 mg, 20.6%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customThe residue obtained by evaporation of the solvent of the filtrate under reduced pressure
  3. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-e425c2dc53fe4ffdb76f563a11d5d571
Source dataset
uspto-grants-2011_02
Patent number
US07884234B2

Reaction notes

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