Water → 3-Chloro-5-(trifluoromethyl)pyridine

HRID 606786

Reaction equation

HRID 606786 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.O.N1C=CC=CC=1CC=O>[Zn].C(O)(=O)C>[Cl:8][C:7]1[CH:2]=[N:3][CH:4]=[C:5]([C:9]([F:11])([F:10])[F:12])[CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 117151722-(Pyridin-2-YL)acetaldehyde

Product 1

HCID 27366983-Chloro-5-(trifluoromethyl)pyridineYield 7.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Add zinc dust (1.18 g) to a suspension of 2,3-dichloro-5-trifluoromethyl-pyridine (2.0 g, 9.30 mmol) in 80:20 water and acetic acid (5 mL) and stir at 90° C. for 1 h. Add more zinc dust (1g) and stir at 90° C. for an additional 15 min. Cool the reaction mixture to room temperature, filter, and wash with dichloromethane. Carefully concentrate and purify the residue by silica gel chromatography, eluting with 100:0 to 0:100 hexane:dichloromethane, to obtain the title compound as a volatile oil (0.120g, 7%).

Workup

  1. stirringstir at 90° C. for an additional 15 min
  2. temperatureCool the reaction mixture to room temperature
  3. filtrationfilter
  4. washwash with dichloromethane
  5. concentrationCarefully concentrate
  6. custompurify the residue by silica gel chromatography
  7. washeluting with 100:0 to 0:100 hexane

Sources & evidence

ORD record
ord-a90e4a127c254a10a0cebcff8276d27e
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Linked notes

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