1-Bromo-3-chloropropane → 1-[(3-Chloropropyl)sulfanyl]-4-methoxybenzene

HRID 344714Notes

Reaction equation

HRID 344714 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:13][CH2:14][CH2:15][Cl:16].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:16][CH2:15][CH2:14][CH2:13][S:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 127654-MethoxybenzenethiolHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate

Product 1

HCID 140058921-[(3-Chloropropyl)sulfanyl]-4-methoxybenzeneYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

With stirring at room temperature, 5.6 g (39.9 mmols) of 4-methoxythiophenol was added by small portions to 20 ml of a solution of 0.98 g (40.8 mmols) of sodium hydride in dimethylformamide. The solution was dropwise added to 40 ml of a solution of 6.3 g (40.0 mmols) of 1-bromo-3-chloropropane in dimethylformamide with stirring under ice cooling. The mixture was stirred under ice cooling for further an hour. After the reaction, an aqueous saturated sodium bicarbonate solution was added to the mixture followed by extraction of the solution with ethyl acetate 3 times. The ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform) to afford 7.8 g (yield: 90%) of the title compound.

Workup

  1. stirringwith stirring under ice cooling
  2. stirringThe mixture was stirred under ice cooling for further an hour
  3. customAfter the reaction
  4. extractionfollowed by extraction of the solution with ethyl acetate 3 times
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-3750c6be80384e9ba636f424f46cc3a5
Source dataset
uspto-grants-1991_10
Patent number
US05053408

Reaction notes

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