Bromine → 2-Bromo-6-(1,3-dioxoisoindolin-2-yl)hexanoic Acid

HRID 966948

Reaktionsgleichung

Reaktionsgleichung von HRID 966948
[C:1]1(=[O:19])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[C:4](=[O:14])[C:3]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:2]12.[Br:20]Br.OS([O-])=O.[Na+].C([O-])(O)=O.[Na+]>O>[Br:20][CH:10]([CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:4](=[O:14])[C:3]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:2]2[C:1]1=[O:19])[C:11]([OH:13])=[O:12]

Komponenten

6

Edukt 4

HCID 24408BromineHCID 781851,3-Dihydro-1,3-dioxo-2H-isoindole-2-hexanoic acidHCID 516892Sodium BicarbonateHCID 23665763Sodium Bisulfite

Produkt 1

HCID 136226402-Bromo-6-(1,3-dioxoisoindolin-2-yl)hexanoic AcidAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Treat dropwise a mixture of 6-phthalimidocaproic acid (12.7 g, 48 mmol) and dry red phosphorous (1.95 g, 63 mmol) with bromine (12.7 mL, 246 mmol) at 0° C. Warm the resulting lumpy mixture to room temperature and heat to 80° C. for 3 hours. Cool the reaction mixture to room temperature, pour into water (300 mL) containing NaHSO3, and neutralize using solid NaHCO3. Wash the aqueous layer with diethyl ether (150 mL) and acidify with concentrated hydrochloric acid. Collect the pale yellow precipitate by filtration and dry to give 2-bromo-6-phthalimidocaproic acid (15 g, 91.5% yield).

Aufarbeitung

  1. additionTreat dropwise
  2. temperatureheat to 80° C. for 3 hours
  3. temperatureCool the reaction mixture to room temperature
  4. washWash the aqueous layer with diethyl ether (150 mL)
  5. customCollect the pale yellow precipitate
  6. filtrationby filtration
  7. customdry

Quellen und Nachweise

ORD-Eintrag
ord-4994cd6bab324fcc93d3c5d25da9512c
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06953788B1

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