Phosphorus tribromide → Methyl 5-(bromomethyl)thiophene-2-carboxylate

HRID 14107

Reaktionsgleichung

Reaktionsgleichung von HRID 14107
O[CH2:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1.P(Br)(Br)[Br:13].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:13][CH2:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 23158735Methyl 5-(hydroxymethyl)thiophene-2-carboxylate

Produkt 1

HCID 11424851Methyl 5-(bromomethyl)thiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-cold solution of methyl 5-(hydroxymethyl)thiophene-2-carboxylate (375 mg, 2.17 mmol) in methylene chloride (9.0 mL) is added phosphorus tribromide (100 μL, 1.08 mmol) and the reaction mixture is stirred at 0° C. for 0.5 h. Saturated sodium bicarbonate (10 mL) is carefully added to the reaction mixture and the phases are separated. The organic phase is washed with water, dried (sodium sulfate), filtered, and concentrated under reduced pressure to yield the title compound in pure form. ESI MS m/z 235 [M+H]+.

Aufarbeitung

  1. customthe phases are separated
  2. washThe organic phase is washed with water
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a9579004e9f04cb59d99e1905f5daad8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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