Dimethylformamide → (2-Bromophenyl)(2,2-diethoxyethyl)sulfane

HRID 275809Notes

Reaction equation

HRID 275809 reaction equation
CN(C=O)C.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[SH:13].C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[CH2:24]Br)[CH3:21]>C(OCC)(=O)C.O>[CH2:20]([O:22][CH:23]([O:26][CH2:27][CH3:28])[CH2:24][S:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[Br:6])[CH3:21]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 805982-Bromobenzenethiol

Product 1

HCID 12045537(2-Bromophenyl)(2,2-diethoxyethyl)sulfaneYield 85.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 500 mL round bottom flask was charged with anhydrous DMF (100 mL), 2-bromothiophenol (10.0 g, 52.88 mmol), potassium carbonate (11.0 g, 79.59 mmol) and bromoacetaldehyde diethyl acetal (8.35 mL, 55.5 mmol). The reaction was stirred at room temperature for 5 hours. Water (50 mL) and ethyl acetate (100 mL) were then added with mixing. The layers were separated and the organic layer was washed with water (5×50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to provide 2-(2-bromophenylthio) acetaldehyde diethyl acetal (13.78 g, 85%).

Workup

  1. additionwith mixing
  2. customThe layers were separated
  3. washthe organic layer was washed with water (5×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5b323118965841bc86b511e091d69000
Source dataset
uspto-grants-2002_03
Patent number
US06353008B1

Reaction notes

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