Cesium carbonate → HCID 86697127, compound

HRID 237555Notes

Reaction equation

HRID 237555 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+].[CH3:17][C:18]1([CH3:25])[CH2:23]OS(=O)[O:20][CH2:19]1>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:17][C:18]([CH3:25])([CH3:23])[CH2:19][OH:20])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 108772941003-85-6

Product 1

HCID 86697127HCID 86697127, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-bromo-3,5-dimethylphenol (625 mg) and Cs2CO3 (5 g) in N,N-dimethylformamide (10 mL) is added 5,5-dimethyl-[1,3,2]dioxathiane-2-oxide (467 mg). The mixture is stirred for 12 hours at 100° C. and then partitioned between water and ethyl acetate. The organic phase is washed with brine and dried (MgSO4). The solvent is evaporated and the residue is purified by HPLC on reversed phase to give the title compound. Yield: 251 mg; LC (method 7): tR=1.16 min; Mass spectrum (ESI+): m/z=287 [M+H]+.

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic phase is washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent is evaporated
  5. customthe residue is purified by HPLC on reversed phase

Sources & evidence

ORD record
ord-a84d3eee0aec43e6a0190e2bef892f7e
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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