Cesium carbonate → HCID 68815247, compound

HRID 732570Notes

Reaction equation

HRID 732570 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([OH:14])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.Cl[C:17]([F:23])([F:22])C(OC)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(C(C)=O)C>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:12]([O:14][CH:17]([F:23])[F:22])[CH:13]=[C:4]([C:3]([O:2][CH3:1])=[O:15])[CH:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 73935Methyl chlorodifluoroacetateHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 68815247HCID 68815247, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

React 5-hydroxy-isophthalic acid dimethyl ester (5.88 g, 28 mmol), methyl 2-chloro-2,2-difluoroacetate (5.9 mL, 56 mmol), cesium carbonate (18.2 g, 56 mmol) in methyl ethyl ketone at reflux for 2 days. Cool to room temperature, filter though a filtering agent, wash with ethyl acetate, concentrate and purify (silica gel chromatography, eluting with 10:90 to 30:70 ethyl acetate:hexanes) to give the title compound (2.7 g, 37%).

Workup

  1. temperatureat reflux for 2 days
  2. filtrationfilter though a filtering agent
  3. washwash with ethyl acetate
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 10:90 to 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-13c8cc8d988f44d4b15c077371c03a0b
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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