p-Chlorothiophenol → 1-Chloro-4-[(2,2-dimethoxyethyl)sulfanyl]benzene

HRID 270007Notes

Reaction equation

HRID 270007 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 141757591-Chloro-4-[(2,2-dimethoxyethyl)sulfanyl]benzeneYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-chlorobenzenethiol (5.78 g; 40 mmol) in anhydrous acetone (50 mL) was added potassium carbonate (5.52 g, 40 mmol) and dropwise at room temperature 2-bromo-1,1-dimethoxy-ethane (4.7 mL, 40 mmol). After 24 h of stirring, the precipitate was filtered, the filtrate concentrated, the residue diluted with water and diethyl ether (150 mL), the organic layer washed successively with water (60 mL), NaOH 4N (30 mL) and water (60 mL), dried over Na2SO4 and concentrated to give 1-chloro-4-(2,2-dimethoxy-ethylsulfanyl)-benzene (compound PRE9) (9.12 g; orange oil) (Yield=98%).

Workup

  1. customdropwise at room temperature
  2. filtrationthe precipitate was filtered
  3. concentrationthe filtrate concentrated
  4. additionthe residue diluted with water and diethyl ether (150 mL)
  5. washthe organic layer washed successively with water (60 mL), NaOH 4N (30 mL) and water (60 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2603a258dd094c48b5caf10334a90edb
Source dataset
uspto-grants-2008_11
Patent number
US07449481B2

Reaction notes

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