Potassium Carbonate → 2-Chloro-5-(4-fluoro-benzyloxy)-quinoline

HRID 2076278Notes

Reaction equation

HRID 2076278 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([Cl:12])=[N:7]2.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>CC(C)=O>[Cl:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[O:1][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([F:19])=[CH:21][CH:22]=2)[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 1354422212-chloroquinolin-5-ol

Product 1

HCID 866194962-Chloro-5-(4-fluoro-benzyloxy)-quinolineYield 48.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Hydroxy-2-chloroquinoline (CAS 124467-35-2, 0.6 g, 3.0 mmol) was dissolved in 15 mL acetone and potassium carbonate (555 mg, 3.0 mmol) was added. Then 4-fluoro-benzylbromide (0.5 ml, 4.0 mmol) was added and the reaction mixture stirred for 18 hours at ambient temperature. The mixture was evaporated and the residue taken up in water and extracted (3×) with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated. The residue was subjected to flash column chromatography on silica gel (heptane/ethyl acetate 90:10->80:20 gradient) to yield 2-chloro-5-(4-fluoro-benzyloxy)-quinoline as a white solid (420 mg, 44%), MS: m/e=289 (M+H+).

Workup

  1. customThe mixture was evaporated
  2. extractionextracted (3×) with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-65cc4096bb694fec8ec3c8ce96e5a2f2
Source dataset
uspto-grants-2011_04
Patent number
US07923561B2

Reaction notes

Loading…