Potassium Carbonate → Methyl 2,4-dichloro-3-[(1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl)oxy]benzoate

HRID 1496624Notes

Reaction equation

HRID 1496624 reaction equation
[Cl:1][C:2]1[C:11]([OH:12])=[C:10]([Cl:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]([F:36])([C:32]([F:35])([F:34])[F:33])[C:22]([F:31])([F:30])[C:23]([F:29])([F:28])[S:24](Cl)(=[O:26])=[O:25]>C(#N)C>[Cl:1][C:2]1[C:11]([O:12][S:24]([C:23]([F:28])([F:29])[C:22]([F:30])([F:31])[C:21]([F:20])([F:36])[C:32]([F:35])([F:34])[F:33])(=[O:26])=[O:25])=[C:10]([Cl:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3249551,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl chlorideHCID 14851232HCID 14851232, compound

Product 1

HCID 118534026Methyl 2,4-dichloro-3-[(1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl)oxy]benzoateYield 16.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

9.5 g (43.0 mmol) of methyl 2,4-dichloro-3-hydroxybenzoate in 240 ml of acetonitrile were admixed with 8.6 g (62.2 mmol) of potassium carbonate and then with 9.5 ml (52.8 mmol) of nonafluoro-n-butanesulfonyl chloride. The reaction mixture was stirred at room temperature (RT) for 16 h. For workup, the contents were poured onto ice-water and the mixture was extracted with ethyl acetate. The organic phase was dried and the filtrate was freed of the solvent on a rotary evaporator. The residue was purified by chromatography, which gave 3.5 g of clean product.

Workup

  1. additionFor workup, the contents were poured onto ice-water
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic phase was dried
  4. customthe filtrate was freed of the solvent on a rotary evaporator
  5. customThe residue was purified by chromatography, which

Sources & evidence

ORD record
ord-bc28b50705364759bba8794d8ece4dc4
Source dataset
uspto-grants-2015_12
Patent number
US09198425B2

Reaction notes

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