4-Bromo-1,1,2-trifluorobut-1-ene → HCID 20058441, compound

HRID 2050529Notes

Reaction equation

HRID 2050529 reaction equation
[SH:1][C:2]1[O:3][C:4]([CH:7]2[CH2:11][CH2:10][CH2:9][O:8]2)=[N:5][N:6]=1.Br[CH2:13][CH2:14][C:15]([F:19])=[C:16]([F:18])[F:17]>O1CCOCC1.CN(C)C=O>[F:19][C:15](=[C:16]([F:18])[F:17])[CH2:14][CH2:13][S:1][C:2]1[O:3][C:4]([CH:7]2[CH2:11][CH2:10][CH2:9][O:8]2)=[N:5][N:6]=1

Participants

5

Reactant 2

HCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 178527953HCID 178527953, compound

Product 1

HCID 20058441HCID 20058441, compoundYield 1,594.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

2.1 g (0.019 mol) of potassium t-butylate are introduced into a solution of 3.2 g (0.018 mol) of 2-mercapto-5-(tetrahydrofuran-2-yl)-1,3,4-oxadiazole in a mixture of 80 ml of 1,4-dioxane and 10 ml of dimethylformamide. 4.9 g (0.026 mol) of 1-bromo-3,4,4-trifluoro-3-butene are then added dropwise at 25° C. and the reaction mixture is stirred at room temperature for 16 hours. The solvent mixture is distilled off under reduced pressure and the residue is dissolved in ethyl acetate. This solution is extracted with water, ice-cold 1 N sodium hydroxide solution and water in succession, dried with sodium sulfate and filtered and the solvent is distilled off under reduced pressure. 80.43 g of the desired product are obtained as a yellow oil (nD27 =1.4904).

Workup

  1. distillationThe solvent mixture is distilled off under reduced pressure
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. extractionThis solution is extracted with water, ice-cold 1 N sodium hydroxide solution and water in succession
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-9ff02882986d4ee9a174a9261d262df3
Source dataset
uspto-grants-1991_05
Patent number
US05013745

Reaction notes

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