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

HRID 2068602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2068602
[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-b57593dda4e8431c94186f1b3f09c094
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299063B2

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