Water → Bromoxynil octanoate

HRID 1111479

Reaktionsgleichung

Reaktionsgleichung von HRID 1111479
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:11])[C:9]=1[OH:10])[C:5]#[N:6].[Cl-].[Na+].O.[C:15](Cl)(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:15]([O:10][C:9]1[C:2]([Br:1])=[CH:3][C:4]([C:5]#[N:6])=[CH:7][C:8]=1[Br:11])(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

7

Edukt 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 8124Octanoyl chlorideHCID 15531Bromoxynil

Produkt 1

HCID 15533Bromoxynil octanoateAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 159952Benzyltributylammonium chlorideKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A mixture of 3,5-dibromo-4-hydroxybenzonitrile (27.69 g) sodium hydroxide (4.08 g), sodium chloride (43.4 g) and water (125 ml) was stirred at room temperature for 15 minutes. Toluene (30 ml) and benzyltributyl ammonium chloride (1.57 g) was added, and a solution of octanoyl chloride (17.06 g) in toluene (30 ml) was slowly added to the stirred mixture over a half an hour while the temperature was maintained at 20° C. After addition was completed, the mixture was stirred for 1 hour and the phases allowed to separate. After removing the aqueous phase, the organic phase was washed with water, then with 5% aqueous Na2O3 and again with water. The solution was dried over Na2O3 and evaporated to dryness, yielding 2,6-dibromo-4-cyanophenyl octanoate (40.08 g, 99.5%) as a brown crystalline solid.

Aufarbeitung

  1. temperaturewas maintained at 20° C
  2. additionAfter addition
  3. stirringthe mixture was stirred for 1 hour
  4. customto separate
  5. customAfter removing the aqueous phase
  6. washthe organic phase was washed with water
  7. customThe solution was dried over Na2O3
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-6b34abb3608d4ff193e9d95799fa4b5f
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04980493

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