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

HRID 72578Notes

Reaction equation

HRID 72578 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-534c33aa1e59440facf12c843a8c0023
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Reaction notes

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