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

HRID 1391471Notes

Reaction equation

HRID 1391471 reaction equation
[OH-].[K+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].Br[CH2:14][CH2:15][CH2:16][Cl:17]>CO>[Cl:17][CH2:16][CH2:15][CH2:14][S:12][C:9]1[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropane2×HCID 14797Potassium HydroxideHCID 158094-Nitrobenzenethiol

Product 1

HCID 149330551-[(3-Chloropropyl)sulfanyl]-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of potassium hydroxide is dissolved in 40 ml of methanol and mixed with 2.3 g of 4-nitrothiophenol. The suspension is stirred for one hour at room temperature and mixed drop by drop with 1.48 ml of 1-bromo-3-chloropropane. After 4 hours of stirring at room temperature, another 0.15 ml of 1-bromo-3-chloropropane is added in drops. The mixture is stirred for 65 hours at room temperature, concentrated by evaporation in a vacuum and taken up in ethyl acetate. It is extracted with water and saturated common salt solution, dried on sodium sulfate and concentrated by evaporation. After purification by flash chromatography, 2.54 g of 1-(3-chloro-propylsulfanyl)-4-nitro-benzene is obtained.

Workup

  1. stirringAfter 4 hours of stirring at room temperature
  2. stirringThe mixture is stirred for 65 hours at room temperature
  3. concentrationconcentrated by evaporation in a vacuum
  4. extractionIt is extracted with water and saturated common salt solution
  5. customdried on sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-93ea9c15ad01461890548213e5dfeb86
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

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