5-Bromo-2-chlorobenzaldehyde → (5-Bromo-2-chloro-phenyl)-[1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinolin-6-yl]-methanol

HRID 72578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 72578
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH2:7][CH2:6][CH2:5]2.C([Li])CCC.[Br:26][C:27]1[CH:28]=[CH:29][C:30]([Cl:35])=[C:31]([CH:34]=1)[CH:32]=[O:33]>C1COCC1>[Br:26][C:27]1[CH:28]=[CH:29][C:30]([Cl:35])=[C:31]([CH:32]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:7][CH2:6][CH2:5]3)[OH:33])[CH:34]=1

Komponenten

5

Edukt 3

HCID 106089255-Bromo-2-chlorobenzaldehydeHCID 583408536-Bromo-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinolineHCID 178418339Butyllithium

Produkt 1

HCID 67115847(5-Bromo-2-chloro-phenyl)-[1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinolin-6-yl]-methanolAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a cooled solution of 6-bromo-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinoline (2.5 g, 7.5 mmol) in THF (30 mL) was added 1.6 M n-butyl lithium in hexanes (4.7 mL, 7.5 mmol) at −78° C., stirred for 30 min. This was transferred to a stirred solution of 5-bromo-2-chlorobenzaldehyde (1.73 g, 7.9 mmol) in THF (30 mL) at −78° C. After stirring for 30 min, reaction was quenched by the addition of saturated aqueous solution of ammonium chloride and extracted with ethyl acetate (2×50 mL). The ethyl acetate layer was washed with water, brine, dried over sodium sulphate, and concentrated. The resulting residue was purified by silica gel column chromatography to give (5-bromo-2-chloro-phenyl)-[1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinolin-6-yl]-methanol (2.31 g).

Aufarbeitung

  1. stirringAfter stirring for 30 min
  2. customreaction
  3. customwas quenched by the addition of saturated aqueous solution of ammonium chloride
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe ethyl acetate layer was washed with water, brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-534c33aa1e59440facf12c843a8c0023
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828951B2

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