Potassium Fluoride → HCID 21946965, compound

HRID 1992774Notes

Reaction equation

HRID 1992774 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8](F)=[O:9].[F-:11].[K+].[C:13]([Si](C)(C)C)([F:16])([F:15])[F:14]>>[F:11][C:2]1([C:8]([OH:9])([C:13]([F:16])([F:15])[F:14])[C:13]([F:16])([F:15])[F:14])[CH2:3][CH:4]2[CH2:7][CH:1]1[CH:6]=[CH:5]2

Participants

4

Reactant 3

HCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 87488765HCID 87488765, compound

Product 1

HCID 21946965HCID 21946965, compoundYield 107%

Procedure

A 100 ml three-necked flask equipped with a thermometer, cooling tube having a 3-way cock and dropping funnel was charged with 27.7 g (168 mmol) of 5-norbornene-2-carboxylic acid fluoride (mixture of endo-form and exo-form) synthesized in Preparation Example 1 and 28 g (482 mmol) of potassium fluoride and was cooled in ice bath in nitrogen gas atmosphere. While maintaining the inside temperature of the flask at 3° to 10° C., 62 g (436 mmol) of CF3SiMe3 was added over two hours with stirring. After increasing the flask temperature to room temperature, stirring was carried out overnight. Then the reaction solution was poured into ice water, followed by extracting with diethylether. After washing an organic phase with water, diluted hydrochloric acid and then saturated sodium bicarbonate solution, the organic phase was dried with calcium chloride. Then refining was carried out by distillation under reduced pressure and 50 g (yield: 80%) of (2-fluoro-5-norbornene-2-yl)-1,1,1,3,3,3-hexafluoro-2-propanol (NB-2) was obtained.

Workup

  1. customA 100 ml three-necked flask equipped with a thermometer
  2. temperaturecooling tube
  3. temperaturewas cooled in ice bath in nitrogen gas atmosphere
  4. temperatureWhile maintaining the inside temperature of the flask at 3° to 10° C.
  5. stirringstirring
  6. extractionby extracting with diethylether
  7. washAfter washing an organic phase with water, diluted hydrochloric acid
  8. dry with materialsaturated sodium bicarbonate solution, the organic phase was dried with calcium chloride
  9. distillationThen refining was carried out by distillation under reduced pressure

Sources & evidence

ORD record
ord-63574cd5ab5a402fb9945b4298bc5a6e
Source dataset
uspto-grants-2010_01
Patent number
US07649118B2

Reaction notes

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