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

HRID 1666447Notes

Reaction equation

HRID 1666447 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[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]([CH3:9])=[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 126484045-Bromo-2-methylphenol

Product 1

HCID 668760572-(5-Bromo-2-methylphenoxy)-5-(trifluoromethyl)pyridineYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-bromo-2-methylphenol (1.0 g, 0.005 mol) in DMF (10 mL) was added K2CO3 (1.38 g, 0.01 mol) at RT. 2-Chloro-5-(trifluoromethyl)pyridine (908 mg, 0.005 mol) was added and the reaction was refluxed at 110° C. for 12 h. The reaction mixture was quenched with water and extracted with EtOAc three times. The organic extract was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure to give the title compound (1.5 g, 88%). 1H NMR (500 MHz, CDCl3): δ 8.42 (s, 1H), 7.92 (d, J=2.15 Hz, 1H), 7.32 (t, J=6.45 1H), 7.23 (d, J=1.5 Hz, 1H), 7.17 (d, J=8.05 Hz, 1H), 7.03 (d, J=8.65 Hz, 1H), 2.12 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc three times
  3. extractionThe 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-72680a9d426c4542a193403c708915a5
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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