1-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-(1H-1,2,4-triazol-1-yl)ethanone → HCID 71258903, compound

HRID 929287Notes

Reaction equation

HRID 929287 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:16](=[O:23])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1.[CH:24]([Mg]Cl)([CH3:26])[CH3:25]>ClCCl.C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:16]([OH:23])([CH:24]([CH3:26])[CH3:25])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1

Participants

5

Reactant 2

HCID 157537781-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-(1H-1,2,4-triazol-1-yl)ethanoneHCID 178418918HCID 178418918, compound

Product 1

HCID 71258903HCID 71258903, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above-mentioned ethanone (120.0 g, 0.34 mol) was added to a solution of MgBr diethyl etherate (195.8 g, 0.76 mol) in dichloromethane (DCM, 2.5 L) and the mixture stirred at room temperature for about 90 min. This mixture was then cooled to about 0° C. and isopropyl magnesium chloride (344.5 mL of a 2 M solution in THF, 0.69 mol) was added dropwise. The mixture was allowed to warm to room temperature and was then quenched by addition of a saturated ammonium chloride solution. The organic components were extracted three times with DCM, the organic phases combined, dried and the solvents evaporated. Addition of MTBE resulted in precipitation of the unreacted starting material, which was filtered off. The filtrate was then purified using reverse phase chromatography to give 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol as a brown oil (31.1 g, 23%, HPLC Rt=1.305 min, masse=392).

Workup

  1. temperatureThis mixture was then cooled to about 0° C.
  2. temperatureto warm to room temperature
  3. customwas then quenched by addition of a saturated ammonium chloride solution
  4. extractionThe organic components were extracted three times with DCM
  5. customdried
  6. customthe solvents evaporated
  7. additionAddition of MTBE
  8. customresulted in precipitation of the
  9. filtrationwas filtered off
  10. customThe filtrate was then purified

Sources & evidence

ORD record
ord-70a5c9b0cf3c4997aa2df3c90f34cd10
Source dataset
uspto-grants-2016_03
Patent number
US09295259B2

Reaction notes

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