Methanol → 6-Bromo-4-chloro-3-(4-fluorobenzyl)-2-methoxyquinoline

HRID 928717Notes

Reaction equation

HRID 928717 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[C:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[C:5]2[Cl:21].[CH3:22][O-:23].[Na+].CO>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:23][CH3:22])[C:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[C:5]2[Cl:21]

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 867155796-Bromo-2,4-dichloro-3-(4-fluorobenzyl)quinoline2×

Product 1

HCID 867155816-Bromo-4-chloro-3-(4-fluorobenzyl)-2-methoxyquinoline

Procedure

A mixture of 6-bromo-2,4-dichloro-3-(4-fluorobenzyl)quinoline (0.350 g, 0.909 mmol, Intermediate 4: step c) and a 0.5 M sodium methoxide in methanol solution (9.09 mL. 4.55 mmol) was stirred at reflux for 16 hours. The mixture was poured into ice water and extracted with EtOAc (2×). The combined EtOAc extract was dried (Na2SO4), filtered and evaporated in vacuo and purified by column chromatography with silica gel (heptane/CH2Cl2) to provide the title compound as a white solid.

Workup

  1. temperatureat reflux for 16 hours
  2. extractionextracted with EtOAc (2×)
  3. extractionThe combined EtOAc extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. custompurified by column chromatography with silica gel (heptane/CH2Cl2)

Sources & evidence

ORD record
ord-dfff30c6bfb54269960db0533d0476bd
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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