Glycerol → 5-Bromo-8-(trifluoromethyl)quinoline

HRID 2097956Notes

Reaction equation

HRID 2097956 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([F:12])([F:11])[F:10])=[C:6]([CH:8]=1)[NH2:7].O[CH2:14][CH:15]([CH2:17]O)O.S(=O)(=O)(O)O>C(OCC)(=O)C.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([F:10])([F:11])[F:12])=[C:6]2[C:8]=1[CH:14]=[CH:15][CH:17]=[N:7]2

Participants

6

Reactant 3

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 250673575-Bromo-2-(trifluoromethyl)aniline

Product 1

HCID 687549745-Bromo-8-(trifluoromethyl)quinolineYield 48%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 5-bromo-2-(trifluoromethyl)aniline (3.0 g, 12.6 mmol), glycerol (4.64 g, 50.0 mmol), and ferrous sulfate (0.56 g, 2.0 mmol) was added conc. sulfuric acid (2.2 mL) dropwise. The reaction mixture was heated at 120° C. for 4 hr. After cooled to RT, the reaction was diluted with ethyl acetate (150 mL), and 2N aq. NaOH was introduced to adjust pH about 13. The organic layer was separated and washed with brine and dried over Na2SO4 and evaporated to give the crude product, which was purified with flash column chromatography to give 5-bromo-8-(trifluoromethyl)quinoline (1.2 g, 48%).

Workup

  1. temperatureAfter cooled to RT
  2. additionwas introduced
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customto give the crude product, which
  8. customwas purified with flash column chromatography

Sources & evidence

ORD record
ord-3915d672e1e743f59b2d87d94aa2f5e0
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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