3-(Trifluoromethyl)phenol → 2-(2-Thienylmethyloxy)-6-(meta-trifluoromethylphenoxy)pyridine

HRID 55119

Reaction equation

HRID 55119 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[N:16]=1>CN(C)C=O.[Cu]I>[S:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[CH2:22][O:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[N:16]=1

Participants

6

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydride2×HCID 181869442-Chloro-6-(2-Thienylmethoxy)Pyridine

Product 1

HCID 199573962-(2-Thienylmethyloxy)-6-(meta-trifluoromethylphenoxy)pyridine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution containing meta-trifluoromethylphenol (3.62 g, 0.0045×5.0 mol), sodium hydride (0.36 g, (Ca.60% in mineral oil), 0.0045×2.0 mol) and CuI (0.42 g, 0.0045×0.5 mol) in dimethylformamide, 2-chloro-6-(2-thienylmethyloxy)pyridine (1.0 g, 0.0045 mol) was added and the resultant solution was refluxed for about 3 hours. Additional sodium hydride (0.36 g, (60% in mineral oil), 0.0045×2.0 mol) was added thereto and the resultant solution was refluxed for another about 1 hour, thereafter the reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate. The obtained organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and thereafter, concentrated and purified on a silica gel column to obtain the end product.

Workup

  1. additionwas added
  2. customthe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
  3. washThe obtained organic layer was washed with aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified on a silica gel column
  7. customto obtain the end product

Sources & evidence

ORD record
ord-cb0f05a242d24a13a620fc4ecb1f7367
Source dataset
uspto-grants-1997_04
Patent number
US05624942

Linked notes

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