Cesium carbonate → HCID 58958576, compound

HRID 915576Notes

Reaction equation

HRID 915576 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:20]([F:26])([F:25])C(OC)=O>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH:20]([F:26])[F:25])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 73935Methyl chlorodifluoroacetateHCID 189336882-broMo-5-hydroxybenzoic acid Methyl ester

Product 1

HCID 58958576HCID 58958576, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 2-bromo-5-hydroxybenzoate (5.63 mmol, 1.30 g) in DMF (8 mL) was added cesium carbonate (11.3 mmol, 3.67 g) and methyl chlorodifluoroacetate (6.75 mmol, 0.71 mL), and the reaction mixture stirred at 90° C. for 16 h. After cooling to rt and dilution with ethyl acetate, the mixture was filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography using hexane/EtOAc (9:1, v/v) as the eluent. The product was obtained as a light yellow oil (560 mg, 35%). GC-MS m/z: 280 (MH+).

Workup

  1. temperatureAfter cooling to rt
  2. filtrationdilution with ethyl acetate, the mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-44695c04dfef4b0e8bfc0e88bfc620bd
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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