Sodium Hydroxide → 5-Chloro-2-(trifluoromethyl)pyridine

HRID 1627726Notes

Reaction equation

HRID 1627726 reaction equation
N([C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[C:5]([C:10]([F:13])([F:12])[F:11])[N:4]=1)N.[OH-].[Na+].Cl[O-].[Na+]>ClCCl>[Cl:9][C:8]1[CH:3]=[N:4][C:5]([C:10]([F:12])([F:11])[F:13])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23665760Sodium Hypochlorite2×HCID 690210312-Hydrazino-3-chloro-6-trifluoromethyl pyridine

Product 1

HCID 135326585-Chloro-2-(trifluoromethyl)pyridineYield 110.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The remaining 2-hydrazino-3-chloro-6-trifluoromethyl pyridine (63.36 g, 0.299 mol) was dissolved in dichloromethane (600 g) and charged to a 2 L, three-neck flask with a mechanical stirrer. Sodium hydroxide (300 g, 1N solution) was added, and sodium hypochlorite (NaCl) (448 g, 0.301 mol, 5% solution) was added in one portion. The solution was stirred for three hours after addition of the sodium hypochlorite, at which point sampling indicated the reaction was complete. The layers were separated, and the aqueous layer was extracted twice with dichloromethane (150 mL). The organic layers were combined, washed with water, dried with magnesium sulfate, filtered, and concentrated on the rotovap to give 60.2 g of 3-chloro-6-trifluoromethyl pyridine.

Workup

  1. additioncharged to a 2 L, three-neck flask with a mechanical stirrer
  2. aliquotat which point sampling
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice with dichloromethane (150 mL)
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated on the rotovap

Sources & evidence

ORD record
ord-c14a721481a040588e8509290e584b5d
Source dataset
uspto-grants-2014_07
Patent number
US08785650B2

Reaction notes

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