Cesium carbonate → Ethyl 2-(4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)phenoxy)acetate

HRID 68307Notes

Reaction equation

HRID 68307 reaction equation
[OH:1][N:2]=[C:3]([C:6]1[CH:18]=[CH:17][C:9]([O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=1)[CH2:4][CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].[F:25][C:26]([F:36])([F:35])[C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1>CN(C=O)C>[F:25][C:26]([F:35])([F:36])[C:27]1[CH:34]=[CH:33][C:30]([CH2:31][O:1][N:2]=[C:3]([C:6]2[CH:18]=[CH:17][C:9]([O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=2)[CH2:4][CH3:5])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 86699619Ethyl 2-(4-(1-(hydroxyimino)propyl)phenoxy)acetate

Product 1

HCID 74371516Ethyl 2-(4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)phenoxy)acetateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of step 2 (18 g, 0.0723 moles) in DMF (54 mL), cesium carbonate (47 gm, 0.1446 moles) and 4-(trifluoromethyl)benzyl bromide (19 gm, 0.0795 moles) were added and the reaction mixture was srirred at 25° C. for 3 hours. 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 28 gm (95%) 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-3d21a13bf6554cea9178ad766188e142
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Reaction notes

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