Cesium carbonate → HCID 57608491, compound

HRID 2390110Notes

Reaction equation

HRID 2390110 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][OH:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:16][CH2:17][OH:18])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 80597m-Bromobenzenethiol

Product 1

HCID 57608491HCID 57608491, compoundYield 90%

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, 52.8 mmol) and 2-bromoethanol (3.90 g, 31.7 mol) and heated to about 50° C. under nitrogen for 12 h. DMF was distilled out completely and the residue was dissolved in DCM and washed with water and brine. Organic layer was dried over Na2SO4, evaporated and purified by column chromatography (silica) to afford 5.5 g (90%) of the title compound as pale yellow solid.

Workup

  1. distillationDMF was distilled out completely
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water and brine
  4. dry with materialOrganic layer was dried over Na2SO4
  5. customevaporated
  6. custompurified by column chromatography (silica)

Sources & evidence

ORD record
ord-d61256767e844daf8906a1533d8e2fa8
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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