Dimethylformamide → 4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-benzaldehyde

HRID 2261745Notes

Reaction equation

HRID 2261745 reaction equation
Br[C:2]1[CH:25]=[CH:24][C:5]([O:6][CH2:7][C:8]2[N:12]([C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:20])[N:11]=[CH:10][C:9]=2[CH:21]([CH3:23])[CH3:22])=[CH:4][C:3]=1[CH3:26].C([Li])CCC.CN(C)[CH:34]=[O:35].[Cl-].[NH4+]>C1COCC1>[Cl:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=1[N:12]1[C:8]([CH2:7][O:6][C:5]2[CH:24]=[CH:25][C:2]([CH:34]=[O:35])=[C:3]([CH3:26])[CH:4]=2)=[C:9]([CH:21]([CH3:23])[CH3:22])[CH:10]=[N:11]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 675277775-(4-Bromo-3-methyl-phenoxymethyl)-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 866354624-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-benzaldehydeYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −78° C. solution of 5-(4-Bromo-3-methyl-phenoxymethyl)-1-(2,6-dichloro-phenyl)-4-isopropyl-1H-pyrazole (906 mg, 2.0 mmol) in anhydrous THF is added 1.6 M n-butyllithium (1.35 mL). After 30 minutes, N,N-dimethylformamide is added (0.5 mL, 6.4 mmol). After 30 minutes, saturated aqueous ammonium chloride is added. The mixture is extracted with ethyl acetate (2×). The combined ethyl acetate layers are dried (MgSO4) and concentrated under reduced pressure. The crude residue is purified via flash chromatography (ethyl acetate/heptane gradient) to afford the title compound (110 mg, 14%). LC-ES/MS m/e 403.0 (M+1).

Workup

  1. waitAfter 30 minutes
  2. extractionThe mixture is extracted with ethyl acetate (2×)
  3. dry with materialThe combined ethyl acetate layers are dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue is purified via flash chromatography (ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-cc4c5d5e933a40e0b9102d392fdc3d90
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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