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Hexane → 2-[p-(2,2-Dibromovinyl)phenyl]-5-pentylpyrimidine

HRID 370681
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 370681
[Br:1][C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([C:30]1[CH:31]=[N:32][C:33]([C:36]2[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=2)=[N:34][CH:35]=1)[CH2:26][CH2:27][CH2:28][CH3:29].CCCCCC>C(Cl)Cl>[Br:1][C:2]([Br:5])=[CH:40][C:39]1[CH:38]=[CH:37][C:36]([C:33]2[N:32]=[CH:31][C:30]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:35][N:34]=2)=[CH:43][CH:42]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8058HexaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 20274898p-(5-Pentyl-2-pyrimidinyl)benzaldehyde

Produkt 1

HCID 202750122-[p-(2,2-Dibromovinyl)phenyl]-5-pentylpyrimidineAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 5.44 g of tetrabromomethane in 80 ml of methylene chloride was placed at 0° C. under argon gasification in a sulphonation flask equipped with a mechanical stirrer and treated within 10 minutes with a solution of 8.6 g of triphenylphosphine in 20 ml of methylene chloride. After completion of the addition, the clear orange solution was stirred at 0° C. for a further 5 minutes and then a solution of 2.08 g of p-(5-pentyl-2-pyrimidinyl)benzaldehyde in 15 ml of methylene chloride was added dropwise within 5 minutes. The mixture was subsequently stirred at 0° C. for a further 30 minutes, then the flask content was poured into 700 ml of hexane and the precipitate which thereby separated was filtered off (rinsing with hexane). The concentrated filtrate was digested with 200 ml of hexane, left to stand at 0° C. for 18 hours, filtered (rinsing with hexane) and the filtrate was concentrated. Low-pressure chromatography (0.5 bar) of the residue (3.7 g) on silica gel with 3% ethyl acetate/petroleum ether gave 2.70 g (80%) of 2-[p-(2,2-dibromovinyl)phenyl]-5-pentylpyrimidine as colourless crystals (purity 94.5%); m.p. 74° C.

Aufarbeitung

  1. customwas placed at 0° C. under argon
  2. customequipped with a mechanical stirrer
  3. additionAfter completion of the addition
  4. stirringThe mixture was subsequently stirred at 0° C. for a further 30 minutes
  5. customthe precipitate which thereby separated
  6. filtrationwas filtered off
  7. wash(rinsing with hexane)
  8. waitleft
  9. waitto stand at 0° C. for 18 hours
  10. filtrationfiltered
  11. wash(rinsing with hexane)
  12. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-277277b7dfbe4a59aa534f7867466867
Quelldatensatz
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04528114

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