Chloroform → N-(3,4,4-trifluoro 3-butenyl)phthalimide

HRID 1710010Notes

Reaction equation

HRID 1710010 reaction equation
Br[CH2:2][CH2:3][C:4]([F:8])=[C:5]([F:7])[F:6].[K].[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C(Cl)(Cl)Cl>CN(C)C=O.O>[F:8][C:4](=[C:5]([F:7])[F:6])[CH2:3][CH2:2][N:14]1[C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]2[C:10]1=[O:20]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6809PhthalimideHCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 5462222Potassium

Product 1

HCID 15239143N-(3,4,4-trifluoro 3-butenyl)phthalimide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 10.0 grams (0.053 mole) of 4-bromo-1,1,2-trifluoro-1-butene in 50 ml of dimethylformamide was added 10.4 grams (0.056) of the commercially available potassium salt of phthalimide. The reaction mixture was warmed to 50° C. where it stirred for four hours. The reaction mixture was allowed to cool and 50 ml of chloroform was added. The mixture was poured into 200 ml of water. The aqueous layer was separated and extracted with two 50 ml portions of chloroform. The combined organic layers were washed with two 50 ml portions of aqueous 5% sodium hydroxide and one 50 ml portion of water. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 4.8 grams of N-(3,4,4-trifluoro-3-butenyl)phthalimide as an oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureto cool
  2. customThe aqueous layer was separated
  3. extractionextracted with two 50 ml portions of chloroform
  4. washThe combined organic layers were washed with two 50 ml portions of aqueous 5% sodium hydroxide and one 50 ml portion of water
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2c08f7bf368e463e866b194b03de9e5c
Source dataset
uspto-grants-1990_08
Patent number
US04952580

Reaction notes

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