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

HRID 2371053Notes

Reaction equation

HRID 2371053 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.CCN(CC)CC.Br[CH2:17][CH:18]([O:21][CH3:22])[O:19][CH3:20].O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:17][CH:18]([O:21][CH3:22])[O:19][CH3:20])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7815p-ChlorothiophenolHCID 8471TriethylamineHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 141757591-Chloro-4-[(2,2-dimethoxyethyl)sulfanyl]benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-chlorobenzenethiol (13 mmol) and Et3N (1.4 g, 13 mmol) in THF (25 mL) at room temperature was added 2-bromo-1,1-dimethoxyethane (2.36 g, 13 mmol) in THF (5 mL). After stirring at room temperature for 30 minutes, the reaction mixture was poured into water (200 mL) and extracted with diethyl ether (3×150 mL). The combined organic layer was dried over Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound.

Workup

  1. extractionextracted with diethyl ether (3×150 mL)
  2. dry with materialThe combined organic layer was dried over Na2SO4
  3. filtrationAfter filtration and concentration
  4. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-16fca2491b9848ab86c53e068e0b93cc
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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