Cesium fluoride → HCID 68458790, compound

HRID 1485850Notes

Reaction equation

HRID 1485850 reaction equation
[C:1]1([C:7]2[C:8]([O:10][C:11](=[O:13])[CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[Cs+].[C:16]([Si](C)(C)C)([F:19])([F:18])[F:17]>C(#N)C.C(OCC)C>[F:17][C:16]([F:19])([F:18])[C:8](=[O:9])[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:12][C:11]([OH:10])=[O:13]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 99174Phenylmaleic anhydrideHCID 552549(Trifluoromethyl)trimethylsilane

Product 1

HCID 68458790HCID 68458790, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of phenylmaleic anhydride (18.7 g, 0.107 mol) in acetonitrile (180 ml) at 0° C. (ice/water/sodium chloride bath—temperature of the bath −10° C.), was added CsF (18.6 g, 0.127 mol), followed by the drop-wise addition of CF3SiMe3 (18.58 ml, 0.127 mol), under nitrogen. The reaction mixture was stirred for 1 h, and was then diluted with diethyl ether and extracted with 2M sodium hydroxide (200 ml). The separated aqueous layer was acidified to pH=1 by the addition of conc. hydrochloric acid. This mixture was extracted with dichloromethane. The separated organic layer was dried (Na2SO4), and the solvent was evaporated in vacuo to yield D1 (22.6 g, 86%) as a mixture of isomers (80/11 ratio by LCMS). C11H7F3O3 requires 244; Found 243 (M-H−).

Workup

  1. extractionextracted with 2M sodium hydroxide (200 ml)
  2. additionThe separated aqueous layer was acidified to pH=1 by the addition of conc. hydrochloric acid
  3. extractionThis mixture was extracted with dichloromethane
  4. dry with materialThe separated organic layer was dried (Na2SO4)
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-f216a84fa29143b4b9accd83c3799390
Source dataset
uspto-grants-2016_08
Patent number
US09422296B2

Reaction notes

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