4-Methoxyphenol → HCID 67386845, compound

HRID 1480729Notes

Reaction equation

HRID 1480729 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10](=[O:12])[CH3:11].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[Br-].[Cu]I>[Cl:1][C:2]1[CH:7]=[C:6]([O:29][C:26]2[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10](=[O:12])[CH3:11]

Participants

7

Reactant 3

HCID 90154-MethoxyphenolHCID 62657Potassium Phosphate, TribasicHCID 58442562HCID 58442562, compound

Product 1

HCID 67386845HCID 67386845, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-chloro-4-iodo-6-methylphenyl)ethanone (1.1 g, 3.7 mmol), K3PO4 (1.6 g, 7.4 mmol), and 4-methoxyphenol (0.55 g, 4.44 mmol) in DMF (55 mL) was added tetrabutylammomium bromide (0.12 g, 0.37 mmol) and copper(I) iodide (70 mg, 0.37 mmol). The reaction was heated at reflux for 22 h. The solution was extracted with EtOAc (10 mL), and the organic layer was separated, washed with H2O (11 mL), dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give 1-[2-chloro-4-(4-methoxyphenoxy)-6-methylphenyl]ethanone as yellow oil in 19% yield: 1H NMR (500 MHz, CDCl3) δ 6.97 (m, 2H), 6.90 (m, 2H), 6.73 (d, J=2.19 Hz, 1H), 6.67 (d, J=1.99 Hz, 1H), 3.81 (s, 3H), 2.52 (s, 3H), 2.20 (s, 3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 22 h
  3. extractionThe solution was extracted with EtOAc (10 mL)
  4. customthe organic layer was separated
  5. washwashed with H2O (11 mL)
  6. dry with materialdried over MgSO4(s)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-2753c8202b9241b494b53cec50a1669b
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

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