4-Methoxybenzenethiol → HCID 86690818, compound

HRID 1465518Notes

Reaction equation

HRID 1465518 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].[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>[Cl:1][C:2]1[CH:7]=[C:6]([S:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10](=[O:12])[CH3:11]

Participants

7

Reactant 3

HCID 127654-MethoxybenzenethiolHCID 14797Potassium HydroxideHCID 58442562HCID 58442562, compound

Product 1

HCID 86690818HCID 86690818, compoundYield 13.5%

Reagents, catalysts & solvents 3

HCID 178419072HCID 178419072, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-chloro-4-iodo-6-methylphenyl)ethanone (3-1, 0.720 g, 2.44 mmol), 4-methoxybenzenethiol (0.45 mL, 3.7 mmol), copper(I) oxide (17.0 mg, 0.12 mmol), and potassium hydroxide (0.34 g, 6.1 mmol) in DMF (2.2 mL) and H2O (0.5 mL) was heated at reflux for 20 h. The mixture was quenched with H2O and extracted with ethyl acetate. The organic layer was collected, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to provide 1-(2-chloro-4-(4-methoxyphenylsulfanyl)-6-methylphenyl)ethanone (3-2, 0.10 g, 0.33 mmol) as yellow oil in 13% yield: 1H NMR (500 MHz, CDCl3) δ 7.44 (d, J=8.7 Hz, 2 H), 6.94 (d, J=8.7 Hz, 2 H), 6.86 (d, J=8.2 Hz, 2 H), 3.85 (s, 3 H), 2.50 (s, 3 H), 2.17 (s, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. customThe mixture was quenched with H2O
  4. extractionextracted with ethyl acetate
  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

Sources & evidence

ORD record
ord-78e8209479ff41dcaf79c484b373c171
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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