Hydrochloric Acid → 3-(4-Bromothiophen-2-yl)acrylic acid

HRID 734308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 734308
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12].N1CCCCC1.Cl>N1C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:10][C:11]([OH:13])=[O:12])[S:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 877924-Bromothiophene-2-carbaldehyde

Produkt 1

HCID 27744523-(4-Bromothiophen-2-yl)acrylic acidAusbeute 115,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The mixture of 4-bromo-thiophene-2-carbaldehyde (10 g, 0.052 mol), malonic acid (6.5 g, 0.063 mol) and piperidine (0.5 ml) in pyridine (40 ml) was stirred for 14 hours at 100° C., which was cooled down to room temperature and poured into water, and resultant mixture was acidified with concentrated HCl. The generated precipitate was collected by filtration, which was suspended with EtOH (50 ml) and water (100 ml). The precipitate was collected by filtration and dried under the reduced pressure to give 3-(4-bromo-thiophen-2-yl)-acrylic acid (14 g). 1H NMR (400 MHz, DMSO-d6) ppm 7.79 (s, 1H), 7.67 (d, J=15.9 Hz, 1H), 7.56 (s, 1H), 6.26 (d, J=15.9 Hz, 1H).

Aufarbeitung

  1. temperaturewhich was cooled down to room temperature
  2. filtrationThe generated precipitate was collected by filtration, which
  3. filtrationThe precipitate was collected by filtration
  4. customdried under the reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-06b3702fa2b440b5bead22d1420ff004
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592352B2

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