Cesium carbonate → HCID 86697153, compound

HRID 237493Notes

Reaction equation

HRID 237493 reaction equation
Br[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][S:5](=[O:10])(=[O:9])[CH2:4]1.[Br:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([OH:19])=[CH:14][C:13]=1[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([O:19][CH2:2][CH:3]2[CH2:8][CH2:7][CH2:6][S:5](=[O:10])(=[O:9])[CH2:4]2)=[CH:14][C:13]=1[CH3:20]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 510722162H-Thiopyran, 3-(bromomethyl)tetrahydro-, 1,1-dioxide

Product 1

HCID 86697153HCID 86697153, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

3-(Bromomethyl)tetrahydro-2H-thiopyrane 1,1-dioxide (1 g) is dissolved in 40 mL of N,N-dimethylformamide. 4-Bromo-3,5-dimethylphenol (885 mg) and cesium carbonate (2.85 g) are added and the reaction mixture is stirred at 130° C. overnight. The reaction mixture is concentrated under vacuum. Water is added and the mixture is extracted with ethyl acetate, The organic phase is separated, dried over sodium sulfate and concentrated under vacuum. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→80:20) to give the title compound. Yield: 800 mg.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. additionWater is added
  3. extractionthe mixture is extracted with ethyl acetate
  4. customThe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→80:20)

Sources & evidence

ORD record
ord-7e38cf6fbf9c4e16a2152b2b2cb7ca57
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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