Hydrochloric Acid → HCID 53416101, compound

HRID 1943878Notes

Reaction equation

HRID 1943878 reaction equation
C([N-]C(C)C)(C)C.[Li+].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[F:16][C:17]([F:24])([F:23])[C:18](OCC)=[O:19].Cl>C1COCC1>[F:16][C:17]([F:24])([F:23])[C:18]([C:15]1[C:10]([F:9])=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 97462-FluoropyridineHCID 9794Ethyl trifluoroacetateHCID 2724682Lithium diisopropylamide

Product 1

HCID 53416101HCID 53416101, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Lithium diisopropylamide (8.2 mL, 14.8 mmol, 1.8M in heptane) was added to THF (20 mL) cooled to −78° C. in a dry ice/acetone bath. 2-Fluoropyridine (1.07 mL, 12.4 mmol) was added dropwise, and the resulting mixture was stirred at −78° C. for 3 hours. Ethyl trifluoroacetate (2.06 mL, 17.2 mmol) was added to the suspension dropwise. The reaction mixture was allowed to slowly warm to room temperature. After 1 hour, the mixture was poured into 1M hydrochloric acid (35 mL) and extracted twice with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over magnesium sulfate, filtered, and evaporated to yield the hydrate of 2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethanone (1.9 g, 90%) as a semisolid.

Workup

  1. temperatureto slowly warm to room temperature
  2. waitAfter 1 hour
  3. extractionextracted twice with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-eb4535dd93dc422a954a9280eac158c6
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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