Cesium fluoride → HCID 68458802, compound

HRID 1630459Notes

Reaction equation

HRID 1630459 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:11][C:12](=[O:14])[CH:13]=2)=[O:10])=[CH:4][CH:3]=1.[F-].[Cs+].[C:17]([Si](C)(C)C)([F:20])([F:19])[F:18]>C(#N)C.C(OCC)C>[F:18][C:17]([F:20])([F:19])[C:9](=[O:10])[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[CH:13][C:12]([OH:11])=[O:14]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 577805HCID 577805, compound

Product 1

HCID 68458802HCID 68458802, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-fluorophenylmaleic anhydride (1.42 g, 7.39 mmol) (prepared by procedures similar to those described in Dean, W. D.; Bum, D. M. J. Org. Chem. 1993, 58, 7916-7917), in acetonitrile (15 ml) at 0° C. (ice/water/sodium chloride bath—temperature of the bath −10° C.), was added CsF (1.1 g, 7.39 mmol), followed by the drop-wise addition of CF3SiMe3 (1 ml, 7.39 mmol), under nitrogen. The reaction mixture was stirred for 1 h, and then diluted with diethyl ether and extracted with 2M sodium hydroxide (200 ml). The organic layer was removed and the aqueous layer acidified to pH=1 by the addition of conc. hydrochloric acid. The mixture was extracted with dichloromethane and the organic layer removed, dried (Na2SO4), and the solvent evaporated in vacuo to yield D5 (1.4 g, 72%) as a mixture of isomers. C11H6F4O3 requires 262 Found 261 (M-H)−.

Workup

  1. extractionextracted with 2M sodium hydroxide (200 ml)
  2. customThe organic layer was removed
  3. additionthe aqueous layer acidified to pH=1 by the addition of conc. hydrochloric acid
  4. extractionThe mixture was extracted with dichloromethane
  5. customthe organic layer removed
  6. dry with materialdried (Na2SO4)
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-cd21babbae66420f8300b2e8b2be8568
Source dataset
uspto-grants-2014_07
Patent number
US08791120B2

Reaction notes

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