1-Chloro-2-iodobenzene → (3-Bromo-2-fluorophenyl)(2-chlorophenyl)methanol

HRID 593737

Reaktionsgleichung

Reaktionsgleichung von HRID 593737
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.C([Mg]Cl)(C)C.[Br:14][C:15]1[C:16]([F:23])=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19]>O1CCCC1>[Br:14][C:15]1[C:16]([F:23])=[C:17]([CH:18]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[OH:19])[CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 119931-Chloro-2-iodobenzeneHCID 220193613-Bromo-2-fluorobenzaldehydeHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 86730399(3-Bromo-2-fluorophenyl)(2-chlorophenyl)methanolAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring solution of 1-chloro-2-iodobenzene (7.05 g, 29.6 mmol) in tetrahydrofuran (Volume: 15 mL) at −15° C. was added isopropylmagnesium chloride (17.24 mL, 34.5 mmol). The mixture was allowed to stir for 30 minutes, at which time 3-bromo-2-fluorobenzaldehyde (5 g, 24.63 mmol) was added. The reaction mixture was stirred overnight. The reaction was quenched with saturated aqueous NH4Cl. The reaction mixture was extracted with EtOAc (3×). The organics were combined, rinsed with brine, dried over Na2SO4, filtered, and concentrated to afford the title compound (7.5 g, 96%).

Aufarbeitung

  1. additionwas added
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. extractionThe reaction mixture was extracted with EtOAc (3×)
  4. washrinsed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-403ace3ff9444bf5bf787d38ecd94229
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242967B2

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