Isophthalic Acid → 5-Bromoisophthalic acid

HRID 870229

Reaktionsgleichung

Reaktionsgleichung von HRID 870229
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=1.[Br:13]N1C(=O)CCC1=O>OS(O)(=O)=O>[Br:13][C:9]1[CH:10]=[C:2]([C:1]([OH:12])=[O:11])[CH:3]=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

Komponenten

4

Edukt 2

HCID 8496Isophthalic AcidHCID 67184N-bromobutanimide

Produkt 1

HCID 900735-Bromoisophthalic acidAusbeute 20,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Into a 100-mL round-bottom flask, was placed a solution of isophthalic acid (10 g, 60.24 mmol, 1.00 equiv) in 98% H2SO4 (60 mL). This was followed by the addition of N-bromosuccinimide (12.80 g, 72.32 mmol, 1.20 equiv), in portions at 60° C. in 10 min. The resulting solution was stirred overnight at 60° C. in an oil bath. The reaction was cooled to room temperature and then quenched by the addition of water/ice. The solids were collected by filtration, and washed with 2×60 mL of hexane. The solid was dried in an oven under reduced pressure. The crude product was purified by re-crystallization from ethyl acetate to give 3 g (20%) of 5-bromoisophthalic acid as a white solid.

Aufarbeitung

  1. customInto a 100-mL round-bottom flask, was placed
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched by the addition of water/ice
  4. filtrationThe solids were collected by filtration
  5. washwashed with 2×60 mL of hexane
  6. customThe solid was dried in an oven under reduced pressure
  7. customThe crude product was purified by re-crystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-63f9f6b9e3bf4afe9e422b6533857578
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969377B2

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