N-bromobutanimide → Methyl 5-bromo-2-methylfuran-3-carboxylate

HRID 383592

Reaktionsgleichung

Reaktionsgleichung von HRID 383592
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][O:7][C:6]=1[CH3:10])=[O:4].C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([Br:18])[O:7][C:6]=1[CH3:10])=[O:4]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 80237Methyl 2-methylfuran-3-carboxylate

Produkt 1

HCID 15534190Methyl 5-bromo-2-methylfuran-3-carboxylateAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

(The following reaction is done under exclusion of light.) Dissolve 2-Methyl-furan-3-carboxylic acid methyl ester (22) (2.00 mL, 15.9 mmol) in chloroform (11 mL) and glacial acetic acid (11 mL) and add NBS (3.85 g, 21.6 mmol) portionwise in between a period of 75 min. Stir the reaction suspension for additional 16 h at rt. Add water to the reaction mixture and extract the aqu. layer with DCM (2 times), wash the combined organic layer with 2M aqu. NaOH, water and brine and dry it with Na2SO4 to obtain 5-Bromo-2-methyl-furan-3-carboxylic acid methyl ester (23) (2.80 g, 80%) as a red brown oil. No further purification. 1H NMR (400 MHz, CDCl3): 2.54 (s, 3H); 3.80 (s, 3H); 6.53 (s, 1H).

Aufarbeitung

  1. custom(The following reaction
  2. extractionAdd water to the reaction mixture and extract the aqu
  3. washlayer with DCM (2 times), wash the combined organic layer with 2M aqu
  4. dry with materialNaOH, water and brine and dry it with Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-2439eb522eb44d7eaf14b632d326e6f7
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367677B2

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