Dimethylformamide → HCID 23505221, compound

HRID 1885053Notes

Reaction equation

HRID 1885053 reaction equation
CC(C)([O-])C.[K+].FC(F)(S([O:22][CH2:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])(=O)=O)C(F)(F)C(F)(F)C(F)(F)F.CN(C=O)C.[Cl:36][C:37]1[C:46](O)=[C:45]([S:48]([CH2:51][CH3:52])(=[O:50])=[O:49])[CH:44]=[CH:43][C:38]=1[C:39]([O:41][CH3:42])=[O:40]>O>[Cl:36][C:37]1[C:46]([O:22][CH2:23][C:24]([F:28])([F:29])[CH:25]([F:26])[F:27])=[C:45]([S:48]([CH2:51][CH3:52])(=[O:50])=[O:49])[CH:44]=[CH:43][C:38]=1[C:39]([O:41][CH3:42])=[O:40]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 15906661HCID 15906661, compoundHCID 235052222,2,3,3-Tetrafluoropropyl nonafluorobutane-1-sulfonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 23505221HCID 23505221, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

1.200 g (4.3 mmol) of potassium tert-butoxide and 1.917 g (4.3 mmol) of 2,2,3,3-tetrafluoropropyl perfluorobutanesulfonate were introduced into 30 ml of DMF in a vessel. At RT, 1200 g (4.3 mol) of methyl 2-chloro-3-hydroxy-4-ethylsulfonylbenzoate were added and the mixture was then heated at 120° C. for 7 h. It was subsequently introduced into water and subjected to extraction with diisopropyl ether. The combined organic phases were washed with water, dried over Na2SO4, and concentrated. Drying under an oil pump vacuum gave methyl 2-chloro-3-(2,2,3,3-tetrafluoropropyloxy)-4-ethylsulfonylbenzoate as a brown oil.

Workup

  1. extractionsubjected to extraction with diisopropyl ether
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customDrying under an oil pump vacuum

Sources & evidence

ORD record
ord-21ca817eed6343f593b0fa19883730cc
Source dataset
uspto-grants-2004_07
Patent number
US06768025B2

Reaction notes

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