Cesium carbonate → HCID 86697130, compound

HRID 237467Notes

Reaction equation

HRID 237467 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].CS([O:11][CH2:12][C:13]([CH3:18])([CH3:17])[CH2:14][O:15][CH3:16])(=O)=O.[Br:19][C:20]1[C:25]([CH3:26])=[CH:24][C:23](O)=[CH:22][C:21]=1[CH3:28]>CN(C)C=O>[Br:19][C:20]1[C:25]([CH3:26])=[CH:24][C:23]([O:11][CH2:12][C:13]([CH3:18])([CH3:17])[CH2:14][O:15][CH3:16])=[CH:22][C:21]=1[CH3:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 86697129HCID 86697129, compound

Product 1

HCID 86697130HCID 86697130, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a microwave vial Cs2CO3 (3.3 g) and KI (50 mg) are added to a solution of 3-methoxy-2,2-dimethylpropyl methanesulfonate (407 mg) and 4-bromo-3,5-dimethylphenol (415 mg) in N,N-dimethylformamide (5 mL). The vial is sealed and the mixture is heated to 120° C. for 12 hours. The mixture is partitioned between ethyl acetate and water. The organic phase is washed with water and brine and is dried (MgSO4). The solvents are evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→80:20). The product thus obtained is purified by HPLC on reversed phase to give the title compound. Yield: 171 mg; LC (method 8): tR=1.02 min; Mass spectrum (ESI+): m/z=301 [M+H]+.

Workup

  1. customThe vial is sealed
  2. customThe mixture is partitioned between ethyl acetate and water
  3. washThe organic phase is washed with water and brine
  4. dry with materialis dried (MgSO4)
  5. customThe solvents are evaporated
  6. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→80:20)
  7. customThe product thus obtained
  8. customis purified by HPLC on reversed phase

Sources & evidence

ORD record
ord-8f038e492cee41b78a89551f754f2075
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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