Chlorodimethylphosphine → Dimethyl(3-nitrobenzyl)phosphane oxide

HRID 1947787

Reaktionsgleichung

Reaktionsgleichung von HRID 1947787
Cl[P:2]([CH3:4])[CH3:3].[O-:5]CC.[Na+].Br[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1>C1COCC1>[CH3:3][P:2](=[O:5])([CH3:4])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1

Komponenten

5

Edukt 3

HCID 69936ChlorodimethylphosphineHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 2723922Sodium ethoxide

Produkt 1

HCID 67256329Dimethyl(3-nitrobenzyl)phosphane oxideAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of chlorodimethylphosphine (250 mg, 2.60 mmol) in THF (0.7 mL) was added dropwise to a stirred suspension of sodium ethoxide (194 mg, 2.85 mmol) in THF (0.8 mL) at 0° C. The resulting mixture was stirred at room temperature for 30 min. then treated with 1-(bromomethyl)-3-nitrobenzene (560 mg, 2.59 mmol). The mixture was then stirred under nitrogen at 100° C. in a sealed tube for 2 h., concentrated in vacuo and the residue purified by chromatography over silica gel eluting with 5% MeOH in dichloromethane to afford 153 mg of dimethyl(3-nitrobenzyl)phosphane oxide (yield: 28%). 1H-NMR (CDCl3, 400 MHz): δ=1.53 (d, J=12.4 Hz, 6H), 3.27 (d, J=14.0 Hz, 2H), 7.55 (t, J=7.6 Hz, 1H), 7.71 (d, J=7.6 Hz, 1H), 8.11 (d, J=2.0 Hz, 1H), 8.16 (dd, J=0.8, 7.2 Hz, 1H). MS (ES+): m/z 214.00 (MH+). HPLC: tR=2.16 min (ZQ3, polar—5 min).

Aufarbeitung

  1. stirringThe mixture was then stirred under nitrogen at 100° C. in a sealed tube for 2 h.
  2. concentrationconcentrated in vacuo
  3. customthe residue purified by chromatography over silica gel eluting with 5% MeOH in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-92df87f53a0442c9b6c8a1addc4b4814
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399433B2

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