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

HRID 1258822Notes

Reaction equation

HRID 1258822 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 67115847(5-Bromo-2-chloro-phenyl)-[1-(4-methoxy-benzyl)-1,2,3,4-tetrahydro-quinolin-6-yl]-methanolYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3fd1b3e9b9ab4ee0aa903dd46dad12a2
Source dataset
uspto-grants-2013_06
Patent number
US08466114B2

Reaction notes

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