Ethyl Acetate → HCID 71236766, compound

HRID 920312Notes

Reaction equation

HRID 920312 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=1[C:19]([F:22])([F:21])[F:20].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>C(#N)C.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=2)=[CH:14][C:13]=1[C:19]([F:20])([F:21])[F:22]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 805204-Chloro-3-(trifluoromethyl)phenolHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 71236766HCID 71236766, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-2-nitropyridine (15 g, 73.9 mmol) and 4-chloro-3-(trifluoromethyl)phenol (14.52 g, 73.9 mmol) in acetonitrile (200 mL) was added potassium carbonate (18.38 g, 133 mmol) and the reaction mixture was stirred at 80° C. for 10 hr. Then, 200 mL of EtOAc and 200 mL of H2O were added. The organic layer was separated and concentrated under reduced pressure. The crude product was purified by a silica gel column chromatography eluting and was eluted with Hex/EtOAc (5:1) to provide 5-(4-chloro-3-(trifluoromethyl)phenoxy)-2-nitropyridine (8 g, 32.8%),

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by a silica gel column chromatography
  4. washeluting
  5. washwas eluted with Hex/EtOAc (5:1)

Sources & evidence

ORD record
ord-618f3b1ddcbd411f9a65395e7b27a043
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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