Nitrogen → 4'-Fluoro-2-(4-trifluoromethylphenyl)acetophenone

HRID 968077

Reaktionsgleichung

Reaktionsgleichung von HRID 968077
N#N.[H-].[Na+].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12](N(C)C)[C:13]#N)=[CH:8][CH:7]=1.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:27]=[CH:26][C:23](CCl)=[CH:22][CH:21]=1.S(=O)(=O)(O)[OH:31]>O.CN(C)C=O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:31])[CH2:13][C:23]2[CH:26]=[CH:27][C:20]([C:19]([F:29])([F:28])[F:18])=[CH:21][CH:22]=2)=[CH:8][CH:7]=1

Komponenten

8

Edukt 5

HCID 947Nitrogen3×HCID 1118Sulfuric AcidHCID 24758Sodium hydrideHCID 123096p-Trifluoromethylbenzyl chlorideHCID 113098562-(4-fluorophenyl)-2-(N,N-dimethylamino)acetonitrile

Produkt 1

HCID 98172164'-Fluoro-2-(4-trifluoromethylphenyl)acetophenoneAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into a 1 l four-necked flask equipped with a thermometer, a stirrer, a dropping funnel and a N2 gas supply tube, a N2 gas was introduced so that the interior of the flask became a N2 atmosphere. 250 ml of dimethylformamide and 16.5 g (0.426 mol) of sodium hydride (62% oil suspension) were charged, and a solution comprising 69 g (0.387 mol) of 2-(4-fluorophenyl)-2-(N,N-dimethylamino)acetonitrile and 75.4 g (0.387 mol) of 4-(trifluoromethyl)benzyl chloride, was dropwise added over a period of one hour at from 10 to 15° C. under cooling with ice water and then further reacted at from 20 to 30° C. for one hour. Then, 280 ml of 40% sulfuric acid was added to this reaction mixture and reacted at from 80 to 90° C. for one hour. After completion of the reaction, 2 l of water was added, and precipitated crystals were collected by filtration and washed with a 2% sodium hydrogen carbonate aqueous solution and water. Then, the crystals were further washed and purified with 100 ml of n-hexane and then vacuum-dried to obtain 97.7 g (yield: 89.4%) of the desired compound (melting point: 93-95° C.) as slightly yellow crystals.

Aufarbeitung

  1. customInto a 1 l four-necked flask equipped with a thermometer, a stirrer, a dropping funnel
  2. customfurther reacted at from 20 to 30° C. for one hour
  3. customreacted at from 80 to 90° C. for one hour
  4. additionwas added
  5. customprecipitated crystals
  6. filtrationwere collected by filtration
  7. washwashed with a 2% sodium hydrogen carbonate aqueous solution and water
  8. washThen, the crystals were further washed
  9. custompurified with 100 ml of n-hexane
  10. customvacuum-dried

Quellen und Nachweise

ORD-Eintrag
ord-407bea5772be4e26a15b15c405f0a3ba
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956132B2

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