Ethyl trifluoroacetate → 2-(7-Chloro-1,3-benzodioxol-5-yl)-4,4,4-trifluoro-3-oxo-butanenitrile

HRID 705704Notes

Reaction equation

HRID 705704 reaction equation
[Na].[Cl:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([CH2:12][C:13]#[N:14])[CH:4]=1.[F:15][C:16]([F:23])([F:22])[C:17](OCC)=[O:18]>C(O)C>[Cl:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([CH:12]([C:17](=[O:18])[C:16]([F:23])([F:22])[F:15])[C:13]#[N:14])[CH:4]=1

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 5360545SodiumHCID 670440102-(7-Chlorobenzo[d][1,3]dioxol-5-yl)acetonitrile

Product 1

HCID 900100662-(7-Chloro-1,3-benzodioxol-5-yl)-4,4,4-trifluoro-3-oxo-butanenitrileYield 112.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Under reflux, 1.7 g of sodium (72.8 mmol) was dissolved in 50 ml of ethanol. At 50° C., a solution of 14.2 g (72.8 mmol) of 2-(7-chloro-1,3-benzodioxol-5-yl)acetonitrile and 10.3 g (72.8 mmol) of ethyl trifluoroacetate in 50 ml of ethanol was added dropwise, and the reaction mixture was then stirred under reflux for 12 hours. After cooling, the reaction mixture was concentrated on a rotary evaporator, dissolved in ethyl acetate and washed twice with 100 ml of 1N hydrochloric acid and once with water. The organic phase was separated off, dried over sodium sulphate, filtered and concentrated to give the title compound (23.9 g; 100%) and used for the next step directly.

Workup

  1. temperatureUnder reflux
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated on a rotary evaporator
  5. dissolutiondissolved in ethyl acetate
  6. washwashed twice with 100 ml of 1N hydrochloric acid and once with water
  7. customThe organic phase was separated off
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-1198d44b1e5a4cd4a110a7a19d545f1b
Source dataset
uspto-grants-2015_11
Patent number
US09174967B2

Reaction notes

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