1-Bromopropane → 1-Bromo-3-propylsulfanylbenzene

HRID 2390108Notes

Reaction equation

HRID 2390108 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][CH2:17][CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH2:16][CH2:17][CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 80597m-Bromobenzenethiol

Product 1

HCID 544502371-Bromo-3-propylsulfanylbenzeneYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 3-bromobenzenethiol (5.00 g, 26.4 mmol) in anhydrous DMF (30 mL) was treated with K2CO3 (7.30 g, 52.8 mmol) followed by 1-bromopropane (3.90 g, 31.7 mmol) and the mixture was heated to about 50° C. under nitrogen for 12 h. The solvent was distilled out completely, and the residue was dissolved in DCM and washed with water and brine. The organic layer was dried over sodium sulphate and evaporated to afford 5.50 g (90%) of the title compound as pale yellow liquid.

Workup

  1. distillationThe solvent was distilled out completely
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-ad0f1809edd549d98b247acd55fe4ebb
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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