Ethyl Acetate → HCID 18614222, compound

HRID 2268120Notes

Reaction equation

HRID 2268120 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:7]=1[CH3:16].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)(=O)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O:1]([C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[O:5][C:6]1[C:7]([CH3:16])=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[CH:10][C:11]=1[CH3:12])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 66827Phenylboronic AcidHCID 18614298HCID 18614298, compound

Product 1

HCID 18614222HCID 18614222, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3-hydroxy-4-methoxyphenoxy)-3,5-dimethylnitrobenzene (150 mg), phenylboronic acid (190 mg), copper (II) acetate (189 mg) and TEA (0.22 mL) in dichloromethane (4 mL) was stirred for 6 h. The reaction was diluted into ethyl acetate, washed with 1N hydrochloric acid, dried over sodium sulfate and concentrated in vacuo. The resulting oil was flash chromatographed (10% DEE/petroleum ether) to afford 4-(3-phenoxy-4-methoxyphenoxy)-3,5-dimethyl-nitrobenzene (130 mg) as a colorless solid.

Workup

  1. washwashed with 1N hydrochloric acid
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customchromatographed (10% DEE/petroleum ether)

Sources & evidence

ORD record
ord-aeadf5eb2d5c4d21b9acaee05bb757ac
Source dataset
uspto-grants-2001_12
Patent number
US06326398B1

Reaction notes

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