Cesium carbonate → HCID 67072133, compound

HRID 1242500Notes

Reaction equation

HRID 1242500 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[F:11])=[O:3].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:19]([CH3:26])([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21].OS([O-])(=O)=O.[K+]>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[C:19]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[C:5]([F:11])[CH:6]=1)([CH3:26])[CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 10796Cesium carbonate2×HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester2×HCID 516920Potassium bisulfateHCID 27249122'-Fluoro-4'-hydroxyacetophenone

Product 1

HCID 67072133HCID 67072133, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 12.0 g (77.9 mmol) of 2-fluoro-4-hydroxyacetophenone, 27.9 g (85.6 mmol) of cesium carbonate and 11.6 ml (77.9 mmol) of ethyl 2-bromo-2-methylpropionate in 200 ml of DMF was heated at 50° C. for 3 days. Twice a day additional 12.7 g (38.9 mmol) of cesium carbonate and 5.8 ml (38.9 mmol) of ethyl 2-bromo-2-methylpropionate were added (total of 2.5 equivalent). The mixture was neutralized with aqueous 10% KHSO4 and extracted with ether (3×). The organic phases were washed with aqueous 10% KHSO4, aqueous 10% NaCl and dried over sodium sulfate. The crude product was purified by flash chromatography over silica gel with heptane/AcOEt 9:1 to 6:1, to give 16.7 g of the title compound as colorless oil.

Workup

  1. extractionextracted with ether (3×)
  2. washThe organic phases were washed with aqueous 10% KHSO4, aqueous 10% NaCl
  3. dry with materialdried over sodium sulfate
  4. customThe crude product was purified by flash chromatography over silica gel with heptane/AcOEt 9:1 to 6:1

Sources & evidence

ORD record
ord-d337037cf8f149b4b5c3bb1cf0bc043e
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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