Hydrochloric Acid → 2-Bromo-3-(2-thienyl)-1-propene

HRID 2413188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2413188
[Br:1][C:2]([CH2:4]Br)=[CH2:3].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[Mg]Br.[Mg].BrC1SC=CC=1.Cl>CC(C)=O.C(=O)=O.CCOCC>[Br:1][C:2]([CH2:4][C:7]1[S:6][CH:10]=[CH:9][CH:8]=1)=[CH2:3]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 105522,3-DibromopropeneHCID 138512-BromothiopheneHCID 5462224MagnesiumHCID 178418438HCID 178418438, Verbindung

Produkt 1

HCID 118305032-Bromo-3-(2-thienyl)-1-propene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 18522661Acetone cardiceLösungsmittel2×

Versuchsvorschrift

A 1000 ml 3-necked round-bottomed flask was fitted with a mechanical stirrer through a mineral oil sealed bearing, a reflux condenser and a 1000 ml addition funnel. A mixture of 70 g of 2,3-dibromopropene and 100 ml of dry ethyl ether was added. The flask was now cooled to 0° C. in acetone/dry-ice and a solution of thienyl magnesium bromide, prepared from 7.8 of magnesium 50 g of 2-bromothiophene (0.31 mol) and 260 ml of dry ether was added at such a rate so that the temperature did not exceed 38° C. The addition took about 1.5 hrs. Stirring was continued and the acetone/dry-ice bath was replaced with a heating mantle. The mixture was gently refluxed for 1.5 hrs. after which time the flask was again cooled and a solution of 5 ml of 36% hydrochloric acid and 200 g of ice were added. The contents of the flask were then transferred to a separatory funnel, and the ether layer was separated and dried over anhydrous sodium sulfate. The ether was distilled off and the residue was fractionated under reduced pressure (65°-78° C./0.5 mm) yielding 41.8 g (67 percent of theory). The residue, 26 g, consisted mainly of diphenyl, m.p. 69°-71° C.

Aufarbeitung

  1. customA 1000 ml 3-necked round-bottomed flask was fitted with a mechanical stirrer through a mineral oil
  2. customsealed
  3. additiona reflux condenser and a 1000 ml addition funnel
  4. additionwas added
  5. additionwas added at such a rate so that the temperature
  6. customdid not exceed 38° C
  7. additionThe addition
  8. temperatureThe mixture was gently refluxed for 1.5 hrs
  9. temperatureafter which time the flask was again cooled
  10. customThe contents of the flask were then transferred to a separatory funnel
  11. customthe ether layer was separated
  12. dry with materialdried over anhydrous sodium sulfate
  13. distillationThe ether was distilled off
  14. customwas fractionated under reduced pressure (65°-78° C./0.5 mm)
  15. customyielding 41.8 g (67 percent of theory)

Quellen und Nachweise

ORD-Eintrag
ord-64516247c33b4a869f0627e0f020b4db
Quelldatensatz
uspto-grants-1985_01
Patentnummer
US04496581

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