Cesium carbonate → 3-(3-Bromophenylsulfanyl)propane-1-ol

HRID 2390109Notes

Reaction equation

HRID 2390109 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:16][CH2:17][CH2:18][OH:19]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:16][CH2:17][CH2:18][OH:19])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 123083-Bromo-1-propanolHCID 80597m-Bromobenzenethiol

Product 1

HCID 585220973-(3-Bromophenylsulfanyl)propane-1-olYield 98.1%

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 Cs2CO3 (17.2 g, 52.9 mmol) followed by 3-bromopropan-1-ol (4.40 g, 31.6 mmol). The mixture was heated to 50° C. under nitrogen for 12 h. DMF was distilled out completely, and the residue was dissolved in DCM and washed with water, brine and dried over Na2SO4. The solvent was evaporated to afford 6.4 g (98%) of the title compound as pale yellow liquid.

Workup

  1. distillationDMF was distilled out completely
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9bf8661431e24bdfbc49231fe41400a2
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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