1-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-(1H-1,2,4-triazol-1-yl)ethanone → HCID 71226383, compound

HRID 704956Notes

Reaction equation

HRID 704956 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.[C:24]([Mg]Br)#[C:25][CH3:26]>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])([C:24]#[C:25][CH3:26])[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1

Participants

4

Reactant 2

HCID 157537781-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-(1H-1,2,4-triazol-1-yl)ethanoneHCID 178419101HCID 178419101, compound

Product 1

HCID 71226383HCID 71226383, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the above-mentioned ethanone (75.5 g, 216.8 mmol) dissolved in THF (450 mL) was added a solution of LaCl3.2LiCl (395.9 mL, 0.6 M in THF) at room temperature and stirred for 1 hour. The resulting solution was added dropwise to 1-propynylmagnesium bromide (650.5 mL, 0.5M in THF) at room temperature. After 1 hour at room temperature, the resulting mixture was quenched with a 10% aqueous solution of HCl and extracted with MTBE. The organic phase was washed with brine, dried and evaporated. The crude compound was stirred in a solution of MTBE/diisopropylether and filtrated to eliminate the starting material. The mother liquors were evaporated and purified on silica gel to give the title compound as a beige solid (31.1 g, HPLC-MS2 Rt=1.15 min, masse=388, m.p=137° C.).

Workup

  1. customthe resulting mixture was quenched with a 10% aqueous solution of HCl
  2. extractionextracted with MTBE
  3. washThe organic phase was washed with brine
  4. customdried
  5. customevaporated
  6. filtrationfiltrated
  7. customThe mother liquors were evaporated
  8. custompurified on silica gel

Sources & evidence

ORD record
ord-2fef54e7b6a146babab8615a9705bb57
Source dataset
uspto-grants-2015_11
Patent number
US09173402B2

Reaction notes

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