Sodium Thiosulfate → (5-Bromo-2-chlorothiophen-3-yl)methanol

HRID 34071Notes

Reaction equation

HRID 34071 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][OH:8].[Br:9]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Br:9][C:4]1[S:3][C:2]([Cl:1])=[C:6]([CH2:7][OH:8])[CH:5]=1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 18938072(2-Chlorothiophen-3-yl)methanol

Product 1

HCID 23070160(5-Bromo-2-chlorothiophen-3-yl)methanolYield 80.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.0 g of (2-chlorothiophen-3-yl)methanol in 60 mL of dimethylformamide was added 3.59 g of N-bromosuccinimide at room temperature, and stirred at this temperature for 2 hours. Adding 10 mL of 10% sodium thiosulfate, and the resultant solution was diluted with ethyl acetate. The organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated, to afford 3.7 g of the title compound as a colorless oil.

Workup

  1. washThe organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f574309933cb4930a12807a587ce64b2
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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