1-Bromo-3-chloropropane → 2-(3-Chloropropylthiomethyl)-thiophene

HRID 361693

Reaction equation

HRID 361693 reaction equation
C[O-].[Na+].[S:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH2:9][SH:10].Br[CH2:12][CH2:13][CH2:14][Cl:15]>CO.C(#N)C.C(OCC)(=O)C>[Cl:15][CH2:14][CH2:13][CH2:12][S:10][CH2:9][C:5]1[S:4][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 80408Thenyl mercaptanHCID 10942334Sodium Methoxide

Product 1

HCID 217148482-(3-Chloropropylthiomethyl)-thiophene

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.5 ml of a 30% sodium methylate solution in methanol is added in drops to 1.0 g of thiophen-2-yl-methanethiol in 8 ml of anhydrous acetonitrile at 0° C. After 5 minutes, the drop-by-drop addition of 1.1 ml of 1-bromo-3-chloropropane is carried out. Then, the reaction solution is allowed to stir for 5 hours at room temperature. For working-up, the batch is diluted with ethyl acetate, washed with water and common salt solution, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Chromatography of the crude product on silica gel with a hexane-ethyl acetate gradient yields 1.3 g of 2-(3-chloropropylthiomethyl)-thiophene as an oil.

Workup

  1. washwashed with water and common salt solution
  2. customdried on magnesium sulfate
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-7024fa252aab4b85ac682ea98518c230
Source dataset
uspto-grants-1999_02
Patent number
US05866560

Linked notes

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