Cesium carbonate → Methyl 2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyridin-2-yl)oxy)acetate

HRID 68311

Reaction equation

HRID 68311 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:19][N:20]=[C:21]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[N:27][CH:28]=1)[CH3:22]>CN(C=O)C>[F:10][C:9]([F:12])([F:11])[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:19][N:20]=[C:21]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[N:27][CH:28]=2)[CH3:22])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 86699620Methyl 2-((5-(1-(hydroxyimino)ethyl)pyridin-2-yl)oxy)acetate

Product 1

HCID 86699621Methyl 2-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)pyridin-2-yl)oxy)acetateYield 102.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(bromomethyl)-4-(trifluoromethyl)benzene (0.87 ml, 5.6 mmoles) in DMF (10 mL), cesium carbonate (3.35 gm, 10.2 mmoles) was added followed by addition of methyl 2-((5-(1-(hydroxyimino)ethyl)pyridin-2-yl)oxy)acetate (1.15 gm, 5.1 mmoles) at 25° C. under nitrogen atmosphere and the reaction mixture was stirred at the same temperature for 12 h. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evapourated under reduced pressure to yield 2.0 gm (94%) of product as thick liquid.

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with water & brine
  5. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-64a3f2c1e9ef42058949e2074cbccac8
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Linked notes

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