Potassium Carbonate → 2-(5-Bromo-2-chlorophenoxy)-5-(trifluoromethyl)pyridine

HRID 1666441Notes

Reaction equation

HRID 1666441 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([CH:7]=1)[O:8][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 8203925-Bromo-2-chlorophenol

Product 1

HCID 641573332-(5-Bromo-2-chlorophenoxy)-5-(trifluoromethyl)pyridineYield 102%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-bromo-2-chlorophenol (1.5 g, 7.23 mmol) in DMF (6 mL) was added potassium carbonate (2.5 g, 18.07 mmol) at RT followed by 2-chloro-5-(trifluoromethyl)pyridine (1.3 g, 7.23 mmol) and the mixture was refluxed at 110° C. for 12 h. The reaction mixture was quenched with water and extracted with ethyl acetate three times. The total organic extract was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure to give the title compound (2.6 g, 100%). 1H NMR (500 MHz, CDCl3): δ 8.38 (s, 1H), 7.95 (d, J=6.5 Hz, 1H), 7.65 (s, 1H), 7.47 (d, J=2 Hz, 1H), 7.12 (m, 2H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate three times
  3. extractionThe total organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a972103174bb44d4a8b3708848301251
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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