Hydrogen Bromide → 1-Bromo-8-hydroxynaphthalene-3,6-disulfonic acid

HRID 269374

Reaktionsgleichung

Reaktionsgleichung von HRID 269374
N[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:9][C:10]=2[OH:12])[CH:5]=[C:4]([S:17]([OH:20])(=[O:19])=[O:18])[CH:3]=1.N([O-])=O.[Na+].[Cl-].[Na+].[BrH:27]>O.[Cu]Br>[Br:27][C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:9][C:10]=2[OH:12])[CH:5]=[C:4]([S:17]([OH:20])(=[O:19])=[O:18])[CH:3]=1

Komponenten

7

Edukt 4

HCID 260Hydrogen Bromide2×HCID 5234Sodium ChlorideHCID 7009H acidHCID 23668193Sodium Nitrite

Produkt 1

HCID 855198901-Bromo-8-hydroxynaphthalene-3,6-disulfonic acidAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24593copper(I) bromideKatalysatorHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

1-Amino-8-hydroxynaphthalene-3,6-disulfonic acid (72% strength, 44.4 g, 0.1 mol) was stirred in a mixture of water (340 mls) and 48% hydrobromic acid (20 mls). The suspension was cooled to 0-5° C. and sodium nitrite (7.6 g, 0.11 mol) was added in small portions. The mixture was stirred for 2 hours at 0-5° C. and then the excess nitrous acid was destroyed by the addition of sulfamic acid solution. Further 48% hydrobromic acid (70 mls) was added and the mixture cooled to 5° C. A solution of copper (I) bromide (14.4 g, 0.1 mol) in 48% hydrobromic acid (30 mls) and water (20 mls) was then added dropwise at 0-5° C. The mixture was stirred for 10 minutes at 5° C. and then the temperature was slowly raised to and maintained at 90° C. for 1 hour. The reaction mixture was cooled to room temperature and sodium chloride added (30% w/v). The product was collected by filtration and washed with 20% sodium chloride solution. The dried product (56 g) contained 49% sodium chloride. Yield 74%.

Aufarbeitung

  1. customthe excess nitrous acid was destroyed by the addition of sulfamic acid solution
  2. additionFurther 48% hydrobromic acid (70 mls) was added
  3. temperaturethe mixture cooled to 5° C
  4. stirringThe mixture was stirred for 10 minutes at 5° C.
  5. temperaturethe temperature was slowly raised to and
  6. temperaturemaintained at 90° C. for 1 hour
  7. temperatureThe reaction mixture was cooled to room temperature
  8. filtrationThe product was collected by filtration
  9. washwashed with 20% sodium chloride solution

Quellen und Nachweise

ORD-Eintrag
ord-9dfec6ede0314f05884ce439909cfa27
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446184B2

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