1-(3-Bromopropoxy)-4-chlorobenzene → 1-Acetylsulfanyl-3-(4-chlorophenoxy)propane

HRID 1840503Notes

Reaction equation

HRID 1840503 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[C:13]([O-:16])(=[S:15])[CH3:14].[K+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:13]([S:15][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)(=[O:16])[CH3:14]

Participants

5

Reactant 3

HCID 2235341-(3-Bromopropoxy)-4-chlorobenzeneHCID 516892Sodium BicarbonateHCID 23670855Potassium ethanethioate

Product 1

HCID 234482731-Acetylsulfanyl-3-(4-chlorophenoxy)propaneYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Intermediate 2 (6.0 g) in DMF (50 ml) was treated with potassium thioacetate (5.7 g) at room temperature for 3 h, then the brown solution was added to 5% sodium bicarbonate solution and extracted with ether (3×200 ml). The solvent was washed with water (200 ml) and brine, dried over MgSO4 and evaporated to give the title compound (5.50 g) as a beige solid.

Workup

  1. extractionextracted with ether (3×200 ml)
  2. washThe solvent was washed with water (200 ml) and brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-eeb8ae6a49374f28b429cae33818e7fd
Source dataset
uspto-grants-2004_01
Patent number
US06680338B2

Reaction notes

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