8-Methylquinoline → 5-Bromo-8-methylquinoline

HRID 2280999Notes

Reaction equation

HRID 2280999 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Br:12]Br>S([O-])([O-])(=O)=O.[Ag+2].OS(O)(=O)=O>[Br:12][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

5

Reactant 2

HCID 119108-MethylquinolineHCID 24408Bromine2×

Product 1

HCID 47150225-Bromo-8-methylquinolineYield 92.4%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 8-Metyl quinoline (30 g, 0.209 mol) in Conc.H2SO4 (300 ml) was added Silver sulphate (97.98 g, 0.314 mol) in lots at 0° C. and followed by Bromine (10.74 ml, 0.209 mol) drop wise for 10 min. After addition of Bromine, the reaction mixture was stirred at RT for 4 h and the reaction completion was confirmed by TLC. After completion of reaction the reaction mixture was quenched with ice and basified with NH4OH solution and extracted with ethyl acetate. The organic layer was washed with water, brine solution and dried over anhydrous sodium sulphate and concentrated to afford (43 g, 92.4% yield) as dark brown liquid. The crude product was as such taken for next step without further purification. 1H NMR (DMSO-d6 400 MHz): δ 8.97-8.96 (dd, J=4.16, 5.8 Hz, 1H), 8.45-8.42 (dd, J=8.56, 10.2 Hz, 1H), 7.81-7.79 (d, J=7.68 Hz, 1H), 7.67-7.64 (dd, J˜8.52, 12.64 Hz, 1H), 7.53-7.51 (dd, J=7.64, 8.52 Hz, 1H), 2.66 (s, 3H).

Workup

  1. customAfter completion of reaction the reaction mixture
  2. customwas quenched with ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customto afford (43 g, 92.4% yield) as dark brown liquid
  8. customas such taken for next step without further purification

Sources & evidence

ORD record
ord-66a43ba4336e4b5e942e34be8bdf21bf
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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