Ethanol → 4-Bromo-2-(diethoxymethyl)thiophene

HRID 40948

Reaktionsgleichung

Reaktionsgleichung von HRID 40948
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.[CH2:9]([OH:11])[CH3:10].[Cl-].[NH4+].C([O-])([O-])O[CH2:16][CH3:17]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]([O:11][CH2:9][CH3:10])[O:8][CH2:16][CH3:17])[S:5][CH:6]=1

Komponenten

5

Edukt 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 877924-Bromothiophene-2-carbaldehydeHCID 53630039Ethylorthoformate

Produkt 1

HCID 122800244-Bromo-2-(diethoxymethyl)thiopheneAusbeute 81 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 4-bromothiophene-2-carbaldehyde (1.2 g, 0.0063 mol) in ethanol (10 mL, 0.2 mol) was treated with ammonium chloride (0.42 g, 0.0078 mol) and ethyl orthoformate (1.2 g, 0.0078 mol). The mixture was stirred at 60° C. for 2 hours. The reaction was quenched with water and extracted with ethyl acetate. The combined organic layer was washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give 4-bromo-2-(diethoxymethyl)thiophene as an oil (1.3 g, 81%). 1H NMR (400 MHz, CDCl3): δ□ 7.22 (s, 1H), 6.99 (s, 1H), 5.68 (s, 1H), 3.63 (q, 4H) 1.24 (t, 6H).

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9c7dc7f272d74b8fa26ea2c736107aea
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530485B2

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