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Sodium Hydroxide → 5-Bromothiophene 2-Oxoacetic Acid

HRID 2260924
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2260924
[Br:1][C:2]1[S:6][C:5]([C:7](=[O:13])[C:8]([O:10]CC)=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO.O>[Br:1][C:2]1[S:6][C:5]([C:7](=[O:13])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 2736376Ethyl (5-bromothiophen-2-yl)(oxo)acetate

Produkt 1

HCID 144525865-Bromothiophene 2-Oxoacetic AcidAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Ethyl 2-(5-bromothien-2-yl)glyoxalate (45.6 g, 173 mmol) from Step A was dissolved in a mixture of 100 mL THF, 100 mL methanol, and 300 mL water, then treated with 10 N NaOH (26 ml, 260 mmol) at room temperature for 20 hours. Volatile solvents were removed by rotary evaporation. The residue was dissolved in 2 L water and extracted with diethyl ether (250 mL). The aqueous layer was acidified to pH 1 with 6 N HCl, and extracted with diethyl ether (3×300 mL). The combined diethyl ether extracts were dried over Na2SO4 and concentrated in vacuo to yield 2-(5-bromothien-2-yl)glyoxalic acid, Intermediate 1 (38.7 g, 95%). The product was then recrystallized from diethyl ether. m.p. 119-120° C.; MS (M−H) 235.1; 1H NMR (300 MHz, CDCl3) d 9.00 (1H, br s), 8.15 (1H, d, J=4.2 Hz), 7.16 (1H, d, J=4.2 Hz); 13C NMR (75 MHz, CDCl3) d 173.80, 159.58, 140.14, 137.17, 132.58, 130.48; IR (KBr) 3326, 3124, 1756, 1634, 1415, 1363, 1308, 1253cm−1;

Aufarbeitung

  1. customVolatile solvents were removed by rotary evaporation
  2. dissolutionThe residue was dissolved in 2 L water
  3. extractionextracted with diethyl ether (250 mL)
  4. extractionextracted with diethyl ether (3×300 mL)
  5. dry with materialThe combined diethyl ether extracts were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a4950dd324504cfea3ecbf55a917da09
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07846671B2

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