Oxalyl chloride → Methyl 2-bromothiophene-3-carboxylate

HRID 604362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604362
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([OH:9])=[O:8].[C:10](Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Komponenten

5

Edukt 2

HCID 65578Oxalyl chlorideHCID 123209712-Bromo-3-thiophenecarboxylic acid

Produkt 1

HCID 53302196Methyl 2-bromothiophene-3-carboxylateAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-bromo-3-thiophene carboxylic acid (1.0 eq, 12.56 g, 60.66 mmol) was suspended in CH2Cl2 (200 ml). Oxalyl chloride (1.1 eq, 5.9 ml, 67.16 mmol) and 5 drops of DMF were added, inducing formation of gas. The mixture was stirred overnight at room temperature and the volatiles were removed in vacuo. The resulting solid was suspended in dry methanol (150 ml) and the mixture heated to ebullition. Evaporation of the solvents afforded methyl 2-bromo-3-thiophene carboxylate (13.16 g, 98% yield) as a crude brown oil. LCMS (ES): 99% pure, m/z not detected; 1H NMR (CDCl3, 400 MHz) δ 3.88 (s, 3H), 7.23 (d, J=5.6, 1H), 7.56 (d, J=5.6, 1H) ppm.

Aufarbeitung

  1. customthe volatiles were removed in vacuo
  2. temperaturethe mixture heated to ebullition
  3. customEvaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-4b1289f312a6478c94e85d2d5f89a29f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910600B2

Notizen zur Reaktion

Wird geladen…