Ammonium Chloride → 1-(4-Chloro-3-fluorophenyl)ethan-1-ol

HRID 1436448

Reaktionsgleichung

Reaktionsgleichung von HRID 1436448
[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[F:13].[NH4+].[Cl-]>O1CCCC1>[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]([OH:10])[CH3:1])=[CH:7][C:6]=1[F:13]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 27249854-Chloro-3-FluorobenzaldehydeHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 219347441-(4-Chloro-3-fluorophenyl)ethan-1-olAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methylmagnesium bromide (22.5 mL, 31.5 mmol; 1.4 M solution in toluene/tetrahydrofuran) was added dropwise to a solution of 4-chloro-3-fluorobenzaldehyde (5.0 g, 31.5 mmol) in 100 mL of dry tetrahydrofuran at −78° C. over 15 min. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into saturated NH4Cl (100 mL). The aqueous layer was extracted with diethyl ether (3×150 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 1-(4-chloro-3-fluorophenyl)ethanol (5.50 g, 100%) as a yellow oil which was used in the next step without further purification, MS (ES) m/z 175 [M+H+].

Aufarbeitung

  1. extractionThe aqueous layer was extracted with diethyl ether (3×150 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3fefa5aa44a8429f9e3956cdbd31434a
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618990B2

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