Potassium Carbonate → 1-Bromo-4-[(2,2-dimethoxyethyl)sulfanyl]benzene

HRID 1013153Notes

Reaction equation

HRID 1013153 reaction equation
[Br: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>[Br: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 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 141757601-Bromo-4-[(2,2-dimethoxyethyl)sulfanyl]benzeneYield 87.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-bromobenzenethiol (7.56 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-bromo-4-(2,2-dimethoxy-ethylsulfanyl)-benzene (compound PRE12) (9.71 g; orange oil) (Yield=87%).

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-7cc92d176527410eb10297ea956a1dce
Source dataset
uspto-grants-2011_07
Patent number
US07981907B2

Reaction notes

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