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Ethyl Acetate → Diethyl 3-(5-bromopyrimidin-2-yloxy)benzylphosphonate

HRID 1666378
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1666378
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]Cl)[CH:10]=2)=[N:6][CH:7]=1.[P:17]([O:24]CC)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20].C(OCC)(=O)C>CCCCCCC>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=2)[CH2:15][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[N:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 31215Triethyl phosphiteHCID 668767225-Bromo-2-(3-(chloromethyl)phenoxy)pyrimidine

Produkt 1

HCID 86623898Diethyl 3-(5-bromopyrimidin-2-yloxy)benzylphosphonateAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8900HeptaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

5-Bromo-2-(3-(chloromethyl)phenoxy)pyrimidine (810 mg, 2.70 mmol) was treated with triethyl phosphite (1 mL, 2.2 mmol), and heated to 150° C. After 16 h, the reaction mixture was removed from the heat and ethyl acetate (about 3 mL) followed by heptane were added. As the reaction mixture cooled an oily precipitate formed. The mixture was made homogenous by addition of ethyl acetate. Heptane was added dropwise until a white solid precipitated. Additional heptane was added and the solid was filtered, washed with heptane and dried in vacuo to afford the title compound (0.737 g, 68% yield) as a white solid. MS (APCI) M+1=401; 1H NMR (400 MHz, CDCl3) δ ppm 1.26 (t, J=6.92 Hz, 6H) 3.18 (d, J=21.64 Hz, 2H) 3.98-4.10 (m, 4H) 7.06-7.11 (m, 1H) 7.15 (q, J=2.01 Hz, 1H) 7.20-7.26 (m, 1H) 7.35-7.42 (m, 1H) 8.56 (s, 2H).

Aufarbeitung

  1. customthe reaction mixture was removed from the
  2. temperatureheat
  3. additionwere added
  4. temperatureAs the reaction mixture cooled an oily precipitate
  5. customformed
  6. customprecipitated
  7. additionAdditional heptane was added
  8. filtrationthe solid was filtered
  9. washwashed with heptane
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2373f4e82567404c9b8598c0a1d00e49
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08044052B2

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