Hydrochloric Acid → HCID 67524108, Verbindung

HRID 2241073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2241073
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6]P(=O)(OCC)OCC)=[CH:4][CH:3]=1.[CH3:17][C:18]([O-])([CH3:20])[CH3:19].[Na+].[CH2:23]([C:27]1([O:51][CH3:52])[C:40]([CH2:43][CH2:44][CH2:45][CH3:46])(OC)[C:39]2[CH:38]=[C:37]([CH:47]=O)[CH:36]=[CH:35][C:34]=2[C:33]2[C:28]1=[CH:29]C(C=O)=C[CH:32]=2)[CH2:24][CH2:25][CH3:26].Cl.CN([CH:57]=[O:58])C>>[Br:1][C:2]1[CH:16]=[CH:19][C:18]([CH:20]=[CH:47][C:37]2[CH:36]=[CH:35][C:34]3[C:33]4[C:28](=[CH:29][C:5]([CH:6]=[CH:6][C:5]5[CH:4]=[CH:3][C:2]([Br:1])=[CH:16][CH:15]=5)=[CH:4][CH:32]=4)[C:27]([CH2:23][CH2:24][CH2:25][CH3:26])([O:51][CH3:52])[C:40]([CH2:43][CH2:44][CH2:45][CH3:46])([O:58][CH3:57])[C:39]=3[CH:38]=2)=[CH:17][CH:3]=1

Komponenten

6

Edukt 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11077666Diethyl (4-Bromobenzyl)phosphonateHCID 23676156Sodium t-butoxideHCID 86611403HCID 86611403, Verbindung

Produkt 1

HCID 67524108HCID 67524108, VerbindungAusbeute 87 %

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

22.9 g (74.7 mmol) of diethyl 4-bromobenzylphosphonate were dissolved in 200 ml of DMF and admixed with 14.4 g (149 mmol) of NaOtBu at about 5° C. under protective gas. After stirring at 5° C. for 30 minutes, 13.9 g (34 mmol) of 9,10-dibutyl-9,10-dimethoxy-9,10-dihydrophenanthrene-2,7-dicarbaldehyde were added at a maximum temperature of 5° C. over a period of 15 minutes and the mixture was subsequently stirred at 5° C. for 1 hour. To work up the mixture, 50 ml of 4M HCl were added dropwise, the precipitate formed was filtered off with suction, washed with water and MeOH and dried. The solid was subsequently recrystallized three times from EtOH/toluene to give 21.1 g (87%) of the monomer having a purity determined by RP-HPLC of 99.8%.

Aufarbeitung

  1. stirringthe mixture was subsequently stirred at 5° C. for 1 hour
  2. additionwere added dropwise
  3. customthe precipitate formed
  4. filtrationwas filtered off with suction
  5. washwashed with water and MeOH
  6. customdried
  7. customThe solid was subsequently recrystallized three times from EtOH/toluene

Quellen und Nachweise

ORD-Eintrag
ord-d0e3f350795045379b158d3b9c7226ba
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723455B2

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