Aluminium lithium hydride → 2-chloro-3-fluoro-N-methylaniline

HRID 1485979

Reaktionsgleichung

Reaktionsgleichung von HRID 1485979
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=1[NH:15][CH:16]=O>C1COCC1>[CH3:16][NH:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:8]=1[Cl:7]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 57346568N-(2-Chloro-3-fluorophenyl)formamide

Produkt 1

HCID 552789582-chloro-3-fluoro-N-methylanilineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of 95% lithium aluminum hydride (2.19 g, 58 mmol) in anhydrous THF (10 mL) at 0° C., was added dropwise a solution of N-(2-chloro-3-fluoro phenyl)-formamide (2.3 g, 13.2 mmol) in anhydrous THF (20 mL). The reaction mixture was allowed to slowly warm to room temperature and was stirred for a further 40 mins. The mixture was cooled to 0° C. and was quenched via the sequential addition of water (4 mL), 15% aq. NaOH (2 mL), then water (4 mL). Organics were extracted into a mixture of 3:1 DCM:IPA (100 mL) and washed with water (50 mL). The organic layer was separated and dried over MgSO4. Filtration then concentration in vacuo gave N-methyl-2-chloro-3-fluoroaniline 29-1 (2.07 g, 99%) as a yellow oil. MS (M+H)+: 160.1, tR=2.21 min (method 1).

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. customwas quenched via the sequential addition of water (4 mL), 15% aq. NaOH (2 mL)
  3. extractionOrganics were extracted into a mixture of 3:1 DCM
  4. washIPA (100 mL) and washed with water (50 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationFiltration
  8. concentrationconcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1fa51c74e6004bcda821e70931dc7942
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422310B2

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