Hydrochloric Acid → HCID 25178693, Verbindung

HRID 1516871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516871
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.C(OP([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Br:26])(=O)OCC)C.CC(C)([O-])C.[K+].Cl>O1CCCC1.O>[Br:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1/[CH:19]=[CH:7]/[C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[OH:10]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 124815-Chloro-salicylaldehydeHCID 12703598Diethyl [(2-bromophenyl)methyl]phosphonateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 25178693HCID 25178693, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

5-Chlorosalicylaldehyde (188 g, 1.2 mol) was added to a solution of (2-bromo-benzyl)-phosphonic acid diethyl ester (369 g, 1.2 mol) in tetrahydrofuran (1500 ml) under nitrogen. A solution of potassium tert-butoxide (300 g, 2.68 mol) in tetrahydrofuran (3000 ml) was added while keeping the temperature at 33° C. After completion of the reaction water (1800 ml) was added followed by 4N HCl (450 ml). The organic layer was washed with sodium carbonate solution (500 ml) and saturated NaCl solution. The organic layer was evaporated under reduced pressure at 50° C. to give trans-2-bromo-5′-chloro-2′-hydroxystilbene (301.9 g, 92%).

Aufarbeitung

  1. customat 33° C
  2. additionwas added
  3. washThe organic layer was washed with sodium carbonate solution (500 ml) and saturated NaCl solution
  4. customThe organic layer was evaporated under reduced pressure at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-1d32674392994d069fbdff3678b17efe
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227623B2

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