Propanoic acid, 2-bromo-2-methyl-, ethyl ester → 2-[5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazol-3-ylmethoxy]-2-methyl-propionic acid ethyl ester

HRID 526706Notes

Reaction equation

HRID 526706 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([CH2:21][OH:22])[C:9]=2[CH3:23])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:26]([O:28][C:29](=[O:34])[C:30](Br)([CH3:32])[CH3:31])[CH3:27]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:26]([O:28][C:29](=[O:34])[C:30]([O:22][CH2:21][C:10]1[C:9]([CH3:23])=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[N:11]=1)([CH3:32])[CH3:31])[CH3:27]

Participants

6

Reactant 3

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 24758Sodium hydrideHCID 16086920[5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazol-3-yl]methanol

Product 1

HCID 899072292-[5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazol-3-ylmethoxy]-2-methyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.6 g of [5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazol-3-yl]-methanol in 15 ml of DMF were added 870 mg of sodium hydride (60% in mineral oil) at room temperature. After 15 min, 1.6 g of tetrabutylammonium iodide and 3.4 g of 2-Bromo-2-methyl-propionic acid ethyl ester were added and the reaction mixture was stirred for 16 h at room temperature. After dilution with saturated aqueous sodium hydrogen carbonate solution the reaction mixture was filtered through a chem Elut® cartridge by eluting with ethyl acetate. The solvents were removed under reduced pressure and the crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 1.3 g.

Workup

  1. filtrationAfter dilution with saturated aqueous sodium hydrogen carbonate solution the reaction mixture was filtered through a chem Elut® cartridge
  2. washby eluting with ethyl acetate
  3. customThe solvents were removed under reduced pressure
  4. customthe crude product was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  5. additionThe fractions containing the product
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-fc1b0cb2b3744cfa97d74cc06ca55ff1
Source dataset
uspto-grants-2016_05
Patent number
US09346762B2

Reaction notes

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