Toluene → 2-Bromo-5-phenyl-thiophene-3-carboxylic acid ethyl ester

HRID 1914540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914540
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:17][CH:18]=1)=[O:13])[CH3:10].C1(C)C=CC=CC=1>C(O)(=O)C>[CH2:9]([O:11][C:12]([C:14]1[CH:15]=[C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:17][C:18]=1[Br:1])=[O:13])[CH3:10]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 67184N-bromobutanimideHCID 58110324Ethyl 5-phenylthiophene-3-carboxylate

Produkt 1

HCID 581102722-Bromo-5-phenyl-thiophene-3-carboxylic acid ethyl esterAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (1.22 g, 6.83 mmol) was added to a solution of ethyl-2-phenylthiophen-4-carboxylate (6.83 mmol) in acetic acid (10 mL) and stirred overnight. Toluene was added and the solvent was removed under vacuum. The product was purified by flash chromatography on silica, eluting with 0%-10% ethyl acetate in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (1.2 g). LCMS m/z 312.52 [M+H]+ R.T.=4.55 mins (Analytical Method 5).

Aufarbeitung

  1. customthe solvent was removed under vacuum
  2. customThe product was purified by flash chromatography on silica
  3. washeluting with 0%-10% ethyl acetate in cyclohexane
  4. additionThe fractions containing the desired product
  5. concentrationwere concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-90eec9a2808348f4a8dd4a7d5f6a494f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614209B2

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