Iodine → 2-(5,6-Dichloro-1H-benzoimidazol-2-yl)-1,1,1-trifluoro-4-methyl-pent-3-en-2-ol

HRID 2273278

Reaktionsgleichung

Reaktionsgleichung von HRID 2273278
[Cl:1][C:2]1[C:16]([Cl:17])=[CH:15][C:5]2[NH:6][C:7]([C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.Br[CH:19]=[C:20]([CH3:22])[CH3:21].II.[Mg]>C1COCC1.C(Cl)Cl>[Cl:17][C:16]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]([OH:14])([CH:19]=[C:20]([CH3:22])[CH3:21])[C:10]([F:13])([F:11])[F:12])=[N:6][C:5]=2[CH:15]=1

Komponenten

7

Edukt 4

HCID 807IodineHCID 985601-Bromo-2-methyl-1-propeneHCID 5462224MagnesiumHCID 115943701-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone

Produkt 1

HCID 237295032-(5,6-Dichloro-1H-benzoimidazol-2-yl)-1,1,1-trifluoro-4-methyl-pent-3-en-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 1-(5,6-dichloro-1H-benzoimidazol-2-yl)-2,2,2-trifluoro-ethanone (565 mg) in THF (5 mL) at 0° C. was added Grignard reagent, which was freshly prepared from 1-bromo-2-methyl-propene (0.51 mL), a small iodine flake, and magnesium powder (146 mg) in THF (5 mL). The resulting mixture was then stirred at room temperature for 3 hr. The reaction was quenched with NH4Cl (sat. aq), filtered through a pad of Celite®, rinsed with EtOAc, the layers were separated, the aqueous layer extracted with EtOAc, dried over Na2SO4, filtered, and concentrated to yield a residue. The residue was purified by flash chromatography with Biotage 40s+ column and elution with 10%-40% EtOAc/hexanes to yield a yellow solid. The yellow solid was dissolved in a minimal amount of CH2Cl2 and triturated with hexanes to yield the title compound as a yellow solid.

Aufarbeitung

  1. customThe reaction was quenched with NH4Cl (sat. aq)
  2. filtrationfiltered through a pad of Celite®
  3. washrinsed with EtOAc
  4. customthe layers were separated
  5. extractionthe aqueous layer extracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a residue
  10. customThe residue was purified by flash chromatography with Biotage 40s+ column and elution with 10%-40% EtOAc/hexanes
  11. customto yield a yellow solid
  12. customtriturated with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f1417769b16040e2b120d996e4479e84
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120830B2

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