1-Bromo-3-chloropropane → Toluene-4-thiosulfonic acid S-(3-chloropropyl)ester

HRID 707674Notes

Reaction equation

HRID 707674 reaction equation
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-:4])(=[O:3])=[S:2].[K+].Br[CH2:14][CH2:15][CH2:16][Cl:17]>CC(C)=O>[Cl:17][CH2:16][CH2:15][CH2:14][S:2][S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 23662126Benzenesulfonothioic acid, 4-methyl-, potassium salt

Product 1

HCID 67607671Toluene-4-thiosulfonic acid S-(3-chloropropyl)ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium thiotosylate (50.0 g, 221 mmol, 1.0 eq.) and 1-bromo-3-chloropropane (38.0 g, 241 mmol, 1.09 eq.) were stirred together in acetone (1 L) at room temperature for 72 hours. The mixture was then concentrated. Next, the mixture was partitioned between dichloromethane and water. The organic solution was washed with brine (2×), dried using MgSO4, concentrated and azeotroped with toluene to produce a pale yellow oil weighing 54 g (92%).

Workup

  1. concentrationThe mixture was then concentrated
  2. customNext, the mixture was partitioned between dichloromethane and water
  3. washThe organic solution was washed with brine (2×)
  4. customdried
  5. concentrationconcentrated
  6. customazeotroped with toluene
  7. customto produce a pale yellow oil

Sources & evidence

ORD record
ord-0426f9cb8c95443eafe75af8829db2b2
Source dataset
uspto-grants-2015_11
Patent number
US09175042B2

Reaction notes

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