Sodium Hydroxide → 5-Bromo-6-fluoro-2-methylquinoline

HRID 1199127Notes

Reaction equation

HRID 1199127 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[Cl-].[Al+3].[Cl-].[Cl-].[Br:17]Br.[OH-].[Na+]>>[Br:17][C:3]1[C:2]([F:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([CH3:12])=[N:8]2

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 707846-Fluoro-2-methylquinolineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 130353135-Bromo-6-fluoro-2-methylquinolineYield 76.6%

Conditions

Temperature
80 °C

Procedure

20.1 g (0.125 mole) of 6-fluoro-2-methylquinoline was added to 25.3 g (0.189 mole) of aluminum chloride at a temperature of 60° C. 19.98 g (0.125 mole) of bromine was added as a gas. The reaction mixture was heated overnight at 80° C. The reaction mixture was then poured onto ice, and 50% aqueous sodium hydroxide was added until the bulk of the solids had dissolved. The mixture was then extracted with toluene. The toluene extract was dried with magnesium sulfate and evaporated under vacuum to give 23 g of 5-bromo-6-fluoro-2-methylquinoline as a light tan solid. The structure was confirmed by nuclear magnetic resonance spectral analysis.

Workup

  1. additionwas added until the bulk of the solids
  2. dissolutionhad dissolved
  3. extractionThe mixture was then extracted with toluene
  4. extractionThe toluene extract
  5. dry with materialwas dried with magnesium sulfate
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-9604b3c7563a4591a64193e01151922e
Source dataset
uspto-grants-1990_02
Patent number
US04898945

Reaction notes

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