Hydrogen Bromide → 1-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone

HRID 545074Notes

Reaction equation

HRID 545074 reaction equation
N[C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.N([O-])=O.[Na+].[BrH:19].[OH-].[Na+]>S(=O)(=O)(O)O.O>[Br:19][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 586455412-Acetyl-5-amino-3-trifluoromethylpyridine

Product 1

HCID 586455621-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 1-(5-amino-3-trifluoromethyl-pyridin-2-yl)-ethanone (408 mg, 2.0 mmol) in 75% sulfuric-acid (6 mL) at 0° C. add sodium nitrite (152 mg, 2.2 mmol) in water (1 mL). Stir the mixture for 30 minutes and add CuBr (343 mg, 2.4 mmol) and 48% HBr (2 mL). Heat the mixture at 60° C. for 30 minutes, cool to 0° C. and basify by dropwise addition of 10M sodium hydroxide. Extract the mixture with ethyl acetate (3×20 mL) and wash the combined organics with brine (50 mL). The organic extract is dried over MgSO4 and the solvent removed under reduced pressure to yield the title compound.

Workup

  1. temperaturecool to 0° C.
  2. extractionExtract the mixture with ethyl acetate (3×20 mL)
  3. washwash the combined organics with brine (50 mL)
  4. extractionThe organic extract
  5. dry with materialis dried over MgSO4
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bbfb7c8913f64d06941b8834c6ce0f39
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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