Cesium carbonate → HCID 57432269, compound

HRID 2264151Notes

Reaction equation

HRID 2264151 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].FC(F)(F)S([O:16][CH2:17][C:18](F)([F:28])[CH2:19]OS(C(F)(F)F)(=O)=O)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:28][CH:18]1[CH2:17][O:16][C:9]2[CH:2]=[CH:3][C:4]([CH:5]=[O:6])=[CH:7][C:8]=2[O:10][CH2:19]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 943653,5-DihydroxybenzaldehydeHCID 86636824HCID 86636824, compound

Product 1

HCID 57432269HCID 57432269, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2 g of 3,5-dihydroxybenzaldehyde, 2.6 g of 2,2-difluoropropane-1,3-diyl bis(trifluoromethanesulfonate) and 10 g of cesium carbonate in 100 mL of anhydrous acetonitrile was heated under nitrogen to 50° C. overnight. The mixture was allowed to cool, then filtered and concentrated under reduced pressure. The residue was partitioned between 250 mL of ethyl acetate and 100 mL of saturated sodium carbonate then dried over magnesium sulfate and concentrated under reduced pressure. Purification by flash chromatography (0-25% ethyl acetate in hexanes) gave the product as white crystalline solid. MS (m+1)=197.1; 1H NMR (400 MHz, CDCl3) 9.82 (s, 1H), 7.45 (m, 2H), 7.05 (d, 1H), 5.1 (doublet of mutliplets, JHF=58 Hz, 1H), 4.5 (m, 4H).

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between 250 mL of ethyl acetate and 100 mL of saturated sodium carbonate
  5. dry with materialthen dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (0-25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-96ac409a8ea748e29211a080e1cd4d67
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

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