Acetic Acid → Thieno(2,3-b)thiophene, 3,4-dibromo-

HRID 1640328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640328
Br[C:2]1[S:11][C:5]2[S:6][C:7](Br)=[C:8]([Br:9])[C:4]=2[C:3]=1[Br:12].C(O)(=O)C>[Zn].O>[Br:9][C:8]1[C:4]2[C:3]([Br:12])=[CH:2][S:11][C:5]=2[S:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 143033Thieno(2,3-b)thiophene, 2,3,4,5-tetrabromo-

Produkt 1

HCID 143030Thieno(2,3-b)thiophene, 3,4-dibromo-Ausbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2,3,4,5-tetrabromothieno[2,3-b]thiophene (0.83 g, 1.8 mmol), zinc dust (0.29 g, 4.4 mmol), and acetic acid (30 ml) is refluxed for 2 h. The reaction mixture is poured into water, extracted with DCM, washed with aqueous saturated sodium carbonate solution, dried (Na2SO4), and concentrated under reduced pressure. The product is purified by recrystallisation from hot methanol to obtain white fibrous crystals (389 mg, 72%). M/Z (298, t, M+). Found C, 24.5; H, 0.8. Calc. for C6H2Br2S2C, 24.2; H, 0.7. 1H NMR (300 MHz, CDCl3) δ 7.32 (s, 2H). 13C NMR (300 MHz, CDCl3) δ 139.35, 137.42, 126.44, 102.96.

Aufarbeitung

  1. temperatureis refluxed for 2 h
  2. extractionextracted with DCM
  3. washwashed with aqueous saturated sodium carbonate solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe product is purified by recrystallisation from hot methanol

Quellen und Nachweise

ORD-Eintrag
ord-727fb6da539442389e9bf6d7b5bf3943
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08114316B2

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