p-Chlorothiophenol → HCID 13642514, compound

HRID 2206815Notes

Reaction equation

HRID 2206815 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:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:16][CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 13642514HCID 13642514, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a 250 mL 2-neck round flask, 4-chlorobenzenethiol (10.0 g, 69 mmol), K2CO3 (9.52 g, 69 mmol), and dimethylformamide (DMF) (100 mL) were poured and stirred, and then 2-bromo-1,1-diethoxyethane (16.3 g, 82.8 mmol) was dissolved in dimethylformamide (100 mL) and gradually added to the aforementioned mixture solution at 0° C. After the reaction, an organic solvent was extracted with ethyl acetate (EtOAc) (250 mL) and water (200 mL), and then dried over MgSO4. After column chromatography using ethyl acetate/petroleum ether (EtOAc/PE=1:60), the solution was distilled in vacuum to give 9.0 g of yellow oil (50% yield).

Workup

  1. additiongradually added to the aforementioned mixture solution at 0° C
  2. customAfter the reaction
  3. extractionan organic solvent was extracted with ethyl acetate (EtOAc) (250 mL) and water (200 mL)
  4. dry with materialdried over MgSO4
  5. distillationthe solution was distilled in vacuum

Sources & evidence

ORD record
ord-82cb008675404f6db2223bcb6dd0a8e6
Source dataset
uspto-grants-2016_06
Patent number
US09373794B2

Reaction notes

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