Diethyl Ether → Flufenpyr-ethyl

HRID 324257Notes

Reaction equation

HRID 324257 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:15](=[O:16])[C:14]([CH3:17])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=[N:11]1.[H-].[Na+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(OCC)C>CN(C)C=O.O>[Cl:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([N:10]2[C:15](=[O:16])[C:14]([CH3:17])=[C:13]([C:18]([F:20])([F:21])[F:19])[CH:12]=[N:11]2)=[CH:4][C:5]=1[O:9][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 99490912-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-methyl-5-(trifluoromethyl)-3(2H)-pyridazinone

Product 1

HCID 3083546Flufenpyr-ethylYield 55.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Then, 3.2 g (9.9 mmol) of 2-[2-fluoro-4-chloro-5-hydroxyphenyl]-4-methyl-5-trifluoromethylpyridazin-3-one was dissolved in about 50 ml of N,N-dimethylformamide, to which 0.44 g (11 mmol) of sodium hydride (60 wt % oil dispersion) was added at room temperature. The mixture was left stand at room temperature for 30 minutes and then cooled with ice, to which 1.8 g (11 mmol) of ethyl bromoacetate was added. The mixture was stirred at room temperature for 1 hour, to which diethyl ether and water were added in this order to make an extraction. The organic layer was washed with 10% aqueous hydrochloric acid solution, saturated aqueous sodium hydrogencarbonate solution, and saturated aqueous sodium chloride solution in this order, and then dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 2.4 g (5.5 mmol) of ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate (compound [1] wherein R is ethyl; hereinafter referred to as compound A), m.p., 102.0° C.

Workup

  1. additionwas added at room temperature
  2. additionwas added
  3. additionwere added in this order
  4. extractionan extraction
  5. washThe organic layer was washed with 10% aqueous hydrochloric acid solution, saturated aqueous sodium hydrogencarbonate solution, and saturated aqueous sodium chloride solution in this order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-f5b86131cf1e4976aafed4f5de3804fa
Source dataset
uspto-grants-2001_04
Patent number
US06218338B1

Reaction notes

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