Cesium carbonate → HCID 86697202, compound

HRID 237539Notes

Reaction equation

HRID 237539 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[Cs+].[Cs+].[O:17]1[C:19]2([CH2:24][CH2:23][S:22][CH2:21][CH2:20]2)[CH2:18]1>CN(C)C=O.O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:18][C:19]2([OH:17])[CH2:24][CH2:23][S:22][CH2:21][CH2:20]2)=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 187531011-Oxa-6-thiaspiro(2.5)octane

Product 1

HCID 86697202HCID 86697202, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (700 mg) in N,N-dimethylformamide (7 mL) is added Cs2CO3 (1.7 g) and 1-oxa-6-thiaspiro[2.5]octane (586 mg). The mixture is stirred for 12 hour at 100° C. The mixture is diluted with water and extracted twice with ethyl acetate. The combined organic phases are washed with water and brine, dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→60:40) to give the title compound. Yield: 986 mg; LC (method 7): tR=1.14 min; Mass spectrum (ESI+): m/z=348 [M+NH4]+.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic phases are washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→60:40)

Sources & evidence

ORD record
ord-639a96b0f51546069b1722dfdf48e51f
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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