Ammonium Chloride → 7-chloro-4-(2-chloroethoxy)-1H-indole

HRID 619326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619326
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([N+:12]([O-])=O)[CH:6]=1.[CH:15]([Mg]Br)=[CH2:16].[NH4+].[Cl-]>C1COCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][Cl:1])=[C:6]2[C:7]=1[NH:12][CH:16]=[CH:15]2

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 107761591-(2-Chloroethoxy)-4-chloro-3-nitrobenzeneHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 106094757-chloro-4-(2-chloroethoxy)-1H-indoleAusbeute 158,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(2-chloroethoxy)-4-chloro-3-nitrobenzene (10.00 g, 0.04236 mol) in THF (230 mL) stirred in a cold bath at -50 to -40° C. was added a THF solution of vinylmagnesium bromide (132 mL, 1.0 M, 0.132 mol) over 2 minutes. After stirring in the cold bath for 2-2.5 hours, saturated NH4Cl (150 mL) was added to the cold solution and it was removed from the cold bath. Enough 1 M HCl was added to dissolve the precipitated solids. This two phase system was stirred for 0.5 hour at most. The layers were separated and the aqueous phase was extracted once with Et2O. Combination of the Et2O and THF followed by drying over MgSO4 and evaporation gave 15.43 g of a dark oil. This was purified by chromatography on silica gel using a three component elutant which consisted of 80% CH2Cl2 and 20% of a gradient of EtOAc/hexane. This gave the product as a yellow solid: 3.32 g (34%); mp 68-72° C. MS EI m/e 229, 231, 233 (M+); 1H NMR (400 MHz, DMSO-d6) δ 3.99 (t, 2H, J=5.1 Hz), 4.34 (t, 2H, J=5.0 Hz), 6.51 (t, 1H, J=2.7 Hz), 6.53 (d, 1H, J=7.8 Hz), 7.04 (d, 1H, J=8.0 Hz), 7.29 (t, 1H, J=2.7 Hz), 11.43 (s, 1H).

Aufarbeitung

  1. customwas removed from the cold bath
  2. additionEnough 1 M HCl was added
  3. dissolutionto dissolve the precipitated solids
  4. stirringThis two phase system was stirred for 0.5 hour at most
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted once with Et2O
  7. dry with materialby drying over MgSO4 and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-f0f34b28c7af4d07bd49b9e7b054d150
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958965

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