Phenolate Sodium → HCID 58615386, compound

HRID 853003Notes

Reaction equation

HRID 853003 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[O-:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+]>C1(O)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 4445035Phenolate SodiumHCID 51395376-Bromo-4-chloroquinoline

Product 1

HCID 58615386HCID 58615386, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 996PhenolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-bromo-4-chloro-quinoline (1.5 g, 6.18 mmol) and sodium phenoxide (2.32 g, 24.74 mmol) in phenol (8.65 g) was heated to 150° C. in a sealed tube and stirred for 15 h. Then, the suspension was diluted with water and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with 1.0N sodium hydroxide (3×50 mL), brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the filtrate was removed under the vacuum and the residue was purified by using a Biotage silica gel column chromatography to afford 1.33 g (71.6% yield) of 6-bromo-4-phenoxy-quinoline as a light brown solid: EI-HRMS m/e calcd for C15H10BrNO (M+) 298.9946, found 298.9946.

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined extracts were washed with 1.0N sodium hydroxide (3×50 mL), brine solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration of the drying agent
  5. customthe filtrate was removed under the vacuum
  6. customthe residue was purified

Sources & evidence

ORD record
ord-907ea29c676a4f32815072be44917832
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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