Cesium carbonate → HCID 69457704, compound

HRID 852411Notes

Reaction equation

HRID 852411 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[C:6]([OH:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].OS([O-])(=O)=O.[K+]>CN(C=O)C>[CH2:24]([O:23][C:21](=[O:22])[C:20]([O:9][C:6]1[CH:5]=[CH:4][C:3]([C:10](=[O:12])[CH3:11])=[C:2]([F:1])[C:7]=1[CH3:8])([CH3:27])[CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 10796Cesium carbonate2×HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester2×HCID 516920Potassium bisulfateHCID 69460450HCID 69460450, compound

Product 1

HCID 69457704HCID 69457704, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 0.21 g (0.62 mmol) of crude 1-(2-fluoro-4-hydroxy-3-methyl-phenyl)-ethanone, 0.45 g (1.37 mmol) of cesium carbonate and 0.24 ml (1.25 mmol) of ethyl 2-bromo-2-methylpropionate in 5 ml of DMF was heated at 50° C. for 7 h. Additional 0.10 g (0.31 mmol) of cesium carbonate and 0.06 ml (0.31 mmol) of ethyl 2-bromo-2-methylpropionate were added and stirred at 50° C. for 11 h. The mixture was neutralized with aqueous 10% KHSO4 and extracted with ether (three times). The organic phases were washed with aqueous 10% KHSO4, aqueous 10% NaCl solution, dried (Na2SO4) and evaporated. The crude product was purified by flash chromatography over silica gel with n-heptane/AcOEt 95:5 to give 0.048 g of the title compound as yellow liquid.

Workup

  1. extractionextracted with ether (three times)
  2. washThe organic phases were washed with aqueous 10% KHSO4, aqueous 10% NaCl solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe crude product was purified by flash chromatography over silica gel with n-heptane/AcOEt 95:5

Sources & evidence

ORD record
ord-3cd667dd152b4b859b07fd76f8994b16
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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