1,4-Dibromobutane → 5-Chloro-3-methyl-6-(pyrrolidin-1-yl)-benzofuran

HRID 637686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 637686
[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]2[C:6]([CH3:9])=[CH:7][O:8][C:4]=2[CH:3]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17]Br.C(N(C(C)C)C(C)C)C>C(O)C>[Cl:12][C:11]1[C:2]([N:1]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:3][C:4]2[O:8][CH:7]=[C:6]([CH3:9])[C:5]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 80561,4-DibromobutaneHCID 81531DiisopropylethylamineHCID 202556476-Amino-5-chloro-3-methylbenzofuran

Produkt 1

HCID 202556495-Chloro-3-methyl-6-(pyrrolidin-1-yl)-benzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 9.1 g (50 mmole) of 6-amino-5-chloro-3-methylbenzofuran, 11.8 ml (0.1 mole) of 1,4-dibromobutane, 17.1 ml (0.1 mole) of N-ethyldiisopropylamine and 60 ml of ethanol is boiled under reflux for 24 hours and then concentrated by evaporation in vacuo. The residue is partitioned between methylene chloride and saturated sodium bicarbonate solution. The crude product obtained after drying and concentration by evaporation of the methylene chloride is chromatographed with petroleum ether/ether over silica gel. Subsequent distillation in a bulb tube (150°/10-1 torr) yields 5-chloro-3-methyl-6-(pyrrolidin-1-yl)-benzofuran having a melting point of 50°-52°.

Aufarbeitung

  1. temperatureunder reflux for 24 hours
  2. concentrationconcentrated by evaporation in vacuo
  3. customThe residue is partitioned between methylene chloride and saturated sodium bicarbonate solution
  4. customThe crude product obtained
  5. customafter drying
  6. concentrationconcentration
  7. customby evaporation of the methylene chloride
  8. customis chromatographed with petroleum ether/ether over silica gel
  9. distillationSubsequent distillation in a bulb tube (150°/10-1 torr)

Quellen und Nachweise

ORD-Eintrag
ord-220f058344494205a4cde4decc2594ca
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04558043

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