4-Methoxybenzenethiol → HCID 58442390, compound

HRID 1465653Notes

Reaction equation

HRID 1465653 reaction equation
I[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.[OH-].[K+]>CN(C=O)C.O.[Cu-]=O>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[CH:3]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 127654-MethoxybenzenethiolHCID 14797Potassium HydroxideHCID 58442513HCID 58442513, compound

Product 1

HCID 58442390HCID 58442390, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-iodo-2,6-dimethylphenyl)ethanone (1.5 g, 5.5 mmol, 1.0 equiv), 4-methoxybenzenethiol (1.01 mL, 8.2 mmol, 1.5 equiv), copper(I) oxide (39.2 mg, 0.3 mmol, 0.05 equiv), and potassium hydroxide (614.1 mg, 11.0 mmol, 2.0 equiv) in DMF (4.4 mL) and H2O (1.1 mL) was heated at reflux for 20 h. The mixture was quenched with H2O (10 mL) and extracted with ether (2×20 mL). The organic layer was collected, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (3.0% EtOAc in hexanes as eluant) to provide 1-(4-(4-methoxyphenylthio)-2,6-dimethylphenyl)ethanone (1.41 g, 4.9 mmol) as yellow oil in 90% yield: 1H NMR (DMSO-d6, 500 MHz) δ 7.39 (d, J=8.5 Hz, 2 H), 6.96 (d, J=8.5 Hz, 2 H), 6.79 (s, 2 H), 3.82 (s, 3 H), 2.43 (s, 3 H), 2.13 (s, 6 H); ESI-MS: m/z 287.6 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. customThe mixture was quenched with H2O (10 mL)
  4. extractionextracted with ether (2×20 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over MgSO4(s)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (3.0% EtOAc in hexanes as eluant)

Sources & evidence

ORD record
ord-16c09d40020a4e1a96f21bbde67c7d99
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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