Triethyl phosphite → Diethyl[(5-bromo-1,3-thiazol-2-yl)methyl]phosphonate

HRID 928123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928123
[Br:1][C:2]1[S:6][C:5]([CH2:7]Br)=[N:4][CH:3]=1.[P:9]([O:16]CC)([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]>C1(C)C=CC=CC=1>[CH2:11]([O:10][P:9]([CH2:7][C:5]1[S:6][C:2]([Br:1])=[CH:3][N:4]=1)(=[O:16])[O:13][CH2:14][CH3:15])[CH3:12]

Komponenten

4

Edukt 2

HCID 31215Triethyl phosphiteHCID 594709305-Bromo-2-(bromomethyl)-1,3-thiazole

Produkt 1

HCID 86720195Diethyl[(5-bromo-1,3-thiazol-2-yl)methyl]phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

5-Bromo-2-(bromomethyl)-1,3-thiazole (1.02 g, 3.97 mmol) and triethyl phosphite (1.389 mL, 7.94 mmol) were combined in toluene (8 mL) and stirred at reflux overnight. The reaction was cooled to room temperature and concentrated in vacuo. The residue was purified by chromatography on silica gel (0-5% methanol in ethyl acetate) to afford diethyl[(5-bromo-1,3-thiazol-2-yl)methyl]phosphonate as a yellow oil. MS ESI calc'd. for C8H14BrNO3PS [M+H]+ 314, 316. found 314, 316. 1H NMR (500 MHz, CDCl3) δ 7.59 (s, 1H), 4.17-4.09 (m, 4H), 3.57 (d, J=21.2 Hz, 2H), 1.32 (t, J=7.1 Hz, 6H).

Aufarbeitung

  1. temperatureat reflux overnight
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (0-5% methanol in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-bef95277b735410194c9b8f242854e50
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290490B2

Notizen zur Reaktion

Wird geladen…